Synthesis, spectroscopic and biological studies of diorganotin(IV) and triorganotin(IV) derivatives...

DOI 10.1515/mgmc-2013-0005 Main Group Met. Chem. 2013; 36(1-2): 49–55

Harminder Kaur* , Jugal Kishore Puri , Jaspreet Kaur and Kanav Dhir

Synthesis, spectroscopic and biological studies of diorganotin(IV) and triorganotin(IV) derivatives of albendazole, ofloxacin and 3-carboxypropyldisulfide Abstract: Diorganotin(IV) and triorganotin(IV) deriva-

tives of the types R 2 SnA (R = n -Bu and n -octyl) and

(R 3 Sn)

2 A (R = n -Bu), where A is the anion of albenda-

zole { methyl[(5-propylsulfanyl-3 H -benzoimidazol-2-yl)

amino]formate } , ofloxacin { ( RS )-7-fluoro-2-methyl-6-(4-

methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.0 5,13 ]

trideca-5(13),6,8,11-tetraene-11-carboxylicacid } and 3-car-

boxypropyldisulfide, have been synthesized. The com-

plexes 1 – 9 obtained were characterized by elemental

analysis as well as infrared (Fourier transform infrared),

nuclear magnetic resonance ( 1 H, 13 C and 119 Sn NMR) and

ultraviolet spectroscopy. On the basis of these spectro-

scopic studies it was proposed that diorganotin complexes

of 3-carboxypropyldisulfide having 1:1 stoichiometry and

complexes of albendazole and ofloxacin having 1:2 stoi-

chiometry show tetrahedral geometry around the tin atom

with monodentate behavior of the carboxylate group in

ofloxacin and 3-carboxypropyldisulfide. Triorganotin

complexes of 3-carboxypropyldisulfide having 1:1 stoi-

chiometry and complexes of ofloxacin and albendazole

having 1:2 stoichiometry show trigonal bipyramidal geom-

etry. The ligand molecule is bound to the Sn atom through

carboxyl oxygen atoms in ofloxacin and 3-carboxypro-

pyldisulfide, and to the nitrogen atom in albendazole. The

biological activity of the synthesized complexes 4 , 5 and 6

has been screened against Candida albicans .

Keywords: albendazole; 3-carboxypropyldisulfide;

Candida albicans ; ofloxacin; organotin.

*Corresponding author: Harminder Kaur, Department of Applied Sciences, PEC University of Technology, Chandigarh 160012, India, e-mail: [email protected] Jugal Kishore Puri: Department of Chemistry, Panjab University, Chandigarh 160014, India Jaspreet Kaur: Department of Biotechnology, University Institute of Engineering and Technology, Panjab University, Chandigarh 160014, India Kanav Dhir: Department of Applied Sciences, PEC University of Technology, Chandigarh 160012, India

Introduction

Extensive use of organotin compounds in various fields

of life results in a quantum leap in organotin chemistry.

The stability and structural diversity of organotin com-

pounds make their coordination chemistry very interest-

ing (Shahzadi and Ali, 2008). One of the most rapidly

developing areas of pharmaceutical research is the dis-

covery of robust drugs for treating cancers. Cisplatin [ cis- diamminedichloroplatinum(II)] (Rosenberg et al., 1965,

1969) is an archetypical metal-based drug widely used for

treating cancer. However, it possesses serious limitations

because of inherent or acquired resistance in tumor cells

and severe side effects (Bonire and Fricker, 2001). There-

fore, there is an exigency to identify effective metal-based

therapeutics, particularly those that overcome inher-

ent and acquired resistance to drug therapy and show

improved therapeutic properties, stimulating the ongoing

investigations of alternative molecule-targeted metal-

based drugs (Storr et al., 2006). Organometallic complexes

of group 14 elements, especially tin(IV) and silicon(IV)

derivatives, have been the subject of considerable interest

(Dakternieks et al., 1997; Casas et al., 2000) owing to their

unique physical, chemical and structural properties (Jain,

1996) favorable to the environment (Ukita et al., 1999).

Recently, we have published a few papers on the chem-

istry of silicon compounds, silatranes and organolead

complexes with amino acids and dipeptides (Sandhu and

Kaur, 1990a,b; Sandhu and Hundal, 1991; Narula et al.,

2000a,b, 2002a,b, 2007; Malhotra et al., 2007; Puri et al.,

2007, 2008a,b, 2009a,b, 2011a,b; Singh et al., 2010a,b).

As all the organotin(IV) derivatives degrade by chemical

action to produce nontoxic inorganic compounds, we are

attempting to explore the chemistry of tin(IV) complexes.

Because fast and effective relief of pain and inflamma-

tion in humans with minimum side effects continues to

be a major challenge for medicinal chemistry research-

ers, many diorganotin(IV) derivatives have been found to

have the potential to be placed in the class of nonsteroidal

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50 H. Kaur et al.: Organotin derivatives of albendazole, ofloxacin and 3-carboxypropyldisulfide

anti-inflammatory drugs (Nath et al., 1999, 2003, 2004a,b,

2006; Shahzadi et al., 2005). Another important applica-

tion of organotin(IV) compounds is their use as activating

agents and templates that combine two functional groups

of the substrate (Puri and Kaur, 2005; Puri et al., 2008a,b).

Ofloxacin is a fluorinated carboxyquinolone and it is a

racemic mixture, which consists of 50% levofloxacin and

50% of its “ mirror image ” or enantiomer dextrofloxacin. It

is used as an antimicrobial agent for oral administration.

Complexes of ofloxacin have been synthesized and char-

acterized with Mg(II), Ca(II), Ba(II), Co(II), Ni(II) and Zn(II)

metal ions (Sagdinc and Bayari, 2004; Affan et al., 2009).

Albendazole is an antihelminthic drug derived from ben-

zimidazole that has a broad spectrum of activity, good tol-

erance and low cost. It has been used against human and

animal helminth parasites. The synthesis and characteriza-

tion of albendazole have been studied with Cu(II), Mn(II),

Ni(II), Co(II) and Cr(III) metal ions (El-Metwaly and Refat,

2011). In the present work, we report the synthesis, spectro-

scopic characterization and biological activities of a series

of di- and triorganotin(IV) complexes of albendazole (L 1 H),

ofloxacin (L 2 H) and 3-carboxypropyldisulfide (L 3 H).

R2SnO+2LnH R2Sn(Ln)2 +H2O

R2SnO+L3H2 R2Sn(L3)+H2O

+2LnH 2R3Sn(Ln)+H2O(R3Sn)2O

+L3H2 (n-Bu)3Sn(L3)+H2O

1; R=n-Bu, n=12; R=n-Octyl, n=14; R=n-Bu, n=2;5; R=n-Octyl, n=2

7; R=n-Bu8; R=n-Octyl

3; R=n-Bu, n=16; R=n-Bu, n=2

9[(n-Bu)3Sn]2O

A

B

C

D

Scheme 1 Azeotropic removal of water for the reaction of di/triorgano-tin oxide with albendazole, ofloxacin and 3-carboxypropyldisulfide. The abbreviation L n refers to the anion of albendazole (n = 1), ofloxacin (n = 2) and 3-carboxypropyldisulfide (n = 3), respectively. All compounds were obtained as crystalline solids. Compounds 4 , 5 and 6 are soluble in chloroform and dichloromethane, whereas compounds 1 , 2 , 3 , 7 , 8 and 9 are soluble in chloroform with one drop of dimethyl sulfoxide.

range 250 – 400 nm. Ofloxacin exhibited one main band at

299 nm, which is attributed to the carbonyl chromophore

group. The slightly longer wavelength bands in the range

NH

NH O

CH3O

SH3CN

NN

H3C

ON COOH

O

F

CH3HO

SS

O

OHO

(L1H) (L2H) (L3H2)

Results and discussion The interaction of R

2 SnO [R = n -Bu and n -octyl] and

(R 3 Sn)

2 O [R = n -Bu] with albendazole, ofloxacin and 3-car-

boxypropyldisulfide in 1:1 and 1:2 (metal/ligand) molar

ratio leads to the formation of complexes ( 1 – 9 ) with an

azeotropic removal of water (Scheme 1). All the synthe-

sized organotin(IV) complexes were obtained in good

yield (67 – 71%) and were stable toward air and moisture.

All the complexes ( 1 – 9 ) were identified by elemental anal-

ysis ( Table 1 ).

Spectroscopic data

Ultraviolet spectra

Ultraviolet (UV) spectra of organotin complexes ( 4 – 6 )

were measured at room temperature in chloroform in the

300 – 310 nm in the organotin(IV) complexes ( 4 – 6 ) are

attributed to a charge transfer transition.

Infrared spectra

Characteristic infrared (IR) frequencies (in cm -1 ) for

organotin(IV) derivatives are presented in Table 2 . The

absence of a broad band due to OH in the 2900 – 3500 cm -1

region of the carboxylic group in complexes 4 – 9 indicates

the deprotonation of this group and confirms its subse-

quent coordination through the oxygen atom and hence the

complex formation (Shahzadi et al., 2007). A strong absorp-

tion appears in the range 414 – 456 cm -1 in the spectra of com-

plexes 4 – 9 (Shahzadi et al., 2008; Shah et al., 2009) but is

absent in the spectra of the free ligand. It is assigned to the

Sn-O stretching vibration, which confirms the coordination

of carboxylate oxygen atoms to tin(IV) (Choudhary et al.,

2002). The presence of a broad band due to the imidazole



H. Kaur et al.: Organotin derivatives of albendazole, ofloxacin and 3-carboxypropyldisulfide 51

-NH group in the spectra of complexes 1 – 3 in the range

3327 – 3337 cm -1 shows the noncoordination of the imidazole

nitrogen around the organotin moiety. The appearance of a

band in the range 423 – 456 cm -1 is assigned to ν (Sn-N) in the

spectra of complexes 1 – 3 . It shows the coordination of nitro-

gen with the organotin moiety. This band is consistent with

that detected in a number of organotin(IV)-oxygen deriva-

tives (Holmes et al., 1987; Sandhu and Hundal, 1991). In com-

plexes 4 – 9 , Δ ν between ν asy

(COO) and ν sym

(COO) is important

because these frequencies can be used to determine the type

of bonding between the metal and the carboxyl groups. The

values of Δ ѵ [ Δ ѵ = ѵ asym

(COO)-ѵ sym

(COO)] can be divided into

three groups: a) in compounds where Δ ѵ (COO) > 350; hence

the compounds contain the high probability of the presence

of monodentate carboxylate group; b) in compounds where

Δ ѵ (COO) < 200; hence the carboxylate groups of the com-

pounds can be considered as bidentate; c) in compounds

where Δ ѵ (COO) < 350 and > 200 are considered as interme-

diate between monodentate and bidentate, which is called

anisobidentate (Lebl et al., 1996). In complexes 4 – 9 , peaks

at 1708 – 1760 and 1330 – 1465 cm -1 have been assigned to the

ν asy

(COO) and ν sym

(COO) groups, respectively. In complexes

4 , 5 , 6 and 9 , the Δ ѵ value corresponds to the monodentate

Table 1 Elemental analysis and some physical properties of organotin(IV) complexes.

Sr. no.

Compound Physical state Melting point ( ° C)

Yield (%)

Molecular formula

Molecular weight

Contents (calcd/found) (%)

C H N

(1) n -Bu 2 Sn(L 1 ) 2 White solid 202 70 C 32 H 46 O 4 N 6 S 2 Sn 761.59 50.47/50.42 6.09/6.11 11.0/11.5 (2) n -Oc 2 Sn(L 1 ) 2 White solid 208 71 C 40 H 62 N 6 O 4 S 2 Sn 873.8 54.98/54.96 7.15/7.13 9.62/9.87 (3) n -Bu 3 Sn(L 1 ) 2 White solid 220 67 C 36 H 55 N 6 O 4 S 2 Sn 818.7 52.81/52.89 6.77/6.70 10.2/10.6 (4) n -Bu 2 Sn(L 2 ) 2 White solid 205 68 C 53 H 87 F 2 N 6 O 8 Sn 532.95 54.04/54.13 6.43/6.45 5.25/5.27 (5) n -Oc 2 Sn(L 2 ) 2 White solid 207 70 C 61 H 103 F 2 N 6 O 8 Sn 645.03 59.53/59.55 7.81/7.86 4.34/4.39 (6) n -Bu 3 Sn(L 2 ) 2 White solid 223 68 C 57 H 96 F 2 N 6 O 8 Sn 590.03 56.95/56.90 7.34/7.30 4.75/4.77 ( 7 ) n -Bu 2 Sn(L 3 ) White solid 210 69 C 16 H 30 O 4 S 2 Sn 469.25 40.95/41.2 6.44/6.42 13.64/13.2 (8) n -Oc 2 Sn(L 3 ) Light Yellow solid 222 70 C 24 H 46 O 4 S 2 Sn 581.46 49.57/49.50 7.97/7.95 11.01/11.14 (9) n -Bu 3 Sn(L 3 ) White solid 225 69 C 20 H 39 O 4 S 2 Sn 526.36 45.64/45.66 7.47/7.55 12.16/12.17

Table 2 Characteristic IR frequencies (in cm -1 ) of di- and triorganotin(IV) derivatives of albendazole, ofloxacin and 3-carboxypropyldisulfide.

Sr. no.

ν (C = O) ν asy (COO) ν sym (COO) ν (Sn-O) ν (Sn-C) ν (C-O)

(1) 1602 563, 596 1268 (2) 1769 562, 597 1270 (3) 1700 565 1278 (4) 1654 1714 1350 456 566, 596 1399 (5) 1657 1711 1345 414 567, 570 1375 (6) 1660 1708 1330 417 568 1370 ( 7 ) 1725 1410 418 562, 575 (8) 1760 1465 419 563, 573 (9) 1735 1380 421 558

behavior of the carboxylate group, whereas in complexes 7

and 8 , the Δ ѵ value shows the anisobidentate nature of the

carboxylic group around the organotin moiety.

Multinuclear ( 1 H and 13 C) NMR spectra

1 H NMR spectra

1 H NMR spectral data of organotin(IV) complexes are pre-

sented in Table 3 . The signal at δ 11.2 ppm due to the car-

boxylic proton in ofloxacin and 3-carboxypropyldisulfide

is absent in the spectra of complexes 4 – 9 . It indicates the

formation of the Sn-O bond and is consistent with the IR

data. The signal in the range δ 5.6 – 5.72 ppm for the imi-

dazole -NH proton in free albendazole does not undergo

any downfield shift on complex formation in 1 – 3 . It shows

the nonparticipation of imidazole nitrogen in bonding to

the central metal ion. The aromatic ring protons in the

range 7.02 – 8.9 ppm in complexes 1 – 6 suffer downfield

shift because of the deshielding of these protons due to

Table 3 1 H NMR chemical shifts ( δ , ppm) of di- and triorganotin(IV) complexes.

Sr. no.

Phenyl protons

-CH 3 -NH Sn-H- α /H- β /H- γ /H- δ up to H- ω

(1) 7.02 – 7.59 3.69 (s, 3H) 5.64 2.58 – 0.93 (2) 7.34 – 7.80 2.78 (s, 3H) 5.72 2.54 – 0.71 (3) 6.00 – 7.06 2.81 (s, 3H) 4.92 2.01 – 0.10 (4) 7.35 – 7.58 3.01 (s, 6H) 1.65 – 0.94 (5) 7.22 – 7.63 3.23 (s, 6H) 1.67 – 1.22 (6) 7.24 – 7.55 2.95 (s, 6H) 1.54 – 0.69 ( 7 ) 2.43 (s, 6H) 2.39 – 0.85 (8) 2.66 (s, 6H) 2.62 – 0.79 (9) 2.41 (s, 6H) 2.81 – 0.94

Sn-CH 2 -CH 2 -CH 2 -CH 3 ; Sn-CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 3 .




the drainage of electron density from ring to metal atom

(Sagdinc and Bayari, 2004; Affan et al., 2009). All the

protons in the complexes 1 – 9 have been identified, and

the total numbers of protons calculated from the integra-

tion curves are in agreement with those calculated by

incremental method (Danish et al., 1995).

13 C NMR spectra

13 C NMR spectral data along with the assignment of

characteristic peaks of all the synthesized organotin(IV)

complexes are presented in Table 4 . The peak at 161.6 –

171.2 ppm has been assigned to the -C = O, which does not

undergo any shift on complexation. It illustrates the non-

participation of this group in complexes 1 – 6 . The signals

in the range 115 – 134 ppm, which have been assigned to

the aromatic carbons of free albendazole and ofloxacin,

suffer significant downfield shift on complexation in

1 – 6 . The appearance of peaks in the range 23.7 – 41.5 ppm,

which has been assigned to the Sn-C peaks of the butyl

and octyl groups, confirms the complex formation in the

complexes 1 – 9 (Sandhu and Kaur, 1990a,b, 1991). All

magnetically nonequivalent carbons of alkyl or phenyl

groups attached to the tin have been identified, and their

chemical shifts are in close agreement with the reported

values.

119 Sn NMR

The possibility of detecting the presence of coordinative

different organotin(IV) moieties was explored by acqui-

sition of 119 Sn NMR spectra. The 119 Sn chemical shifts

usually cover a range, quoted relative to tetramethyltin,

with increasing coordination number of tin producing a

Table 4 13 C NMR spectral data of di- and triorganotin(IV) complexes.

Sr. no.

C == O -COO Ph-C Sn-(C- α to C- ω )

(1) 168.8 121.7 – 109.9 40.1 – 37.3 (2) 171.2 124.9 – 111.0 40.2 – 39.1 (3) 169.7 120.9 – 112.8 40.5 – 38.3 (4) 160.5 172.1 115.7 – 131.0 40.1 – 38.8 (5) 161.6 173.4 117.9 – 132.8 40.3 – 38.6 (6) 165.8 171.7 117.2 – 134.8 40.0 – 38.4 ( 7 ) 172.3, 182.7 – 27.2 – 24.0 (8) – 171.6, 183.8 – 28.4 – 25.6 (9) – 176.6, 185.5 – 29.7 – 23.7

Sn-CH 2 -CH 2 -CH 2 -CH 3 ; Sn-CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 2 -CH 3 .

large upfield shift for δ ( 119 Sn). 119 Sn NMR spectral data of

complex 7 depicted a single resonance signal at δ value

-143. As indicated by the single value, trigonal bipyrami-

dal geometry around the tin atom is proposed in this poly-

meric structure (Holecek et al., 1986).

Antifungal activity

The synthesized complexes ( 1 – 9 ) are checked in dimethyl

sulfoxide, chloroform, methanol, ethanol and dichlo-

romethane for their solubility, but the complexes ( 4 – 6 )

are soluble in CHCl 3 . The complexes ( 4 – 6 ) are screened

against Candida albicans for their antifungal activity.

Percentage inhibition of complexes ( 4 – 6 ) is presented in

Table 5 . Triorganotin(IV) complex ( 6 ) is found to be more

active than diorganotin(IV) derivatives ( 4 – 5 ).

Conclusion Organotin(IV) complexes of albendazole, ofloxacin and

3-carboxypropyldisulfide have been synthesized in 1:1

and 1:2 (metal: ligand) molar ratio through azeotropic

removal of water. The spectroscopic studies of all the

synthesized complexes suggest a tetrahedral geometry

in diorganotin complexes of albendazole and ofloxacin,

whereas trigonal bipyramidal in 3-carboxypropyldi-

sulfide (Holecek et al., 1986; Lebl et al., 1996). In trior-

ganotin complexes of albendazole, ofloxacin and 3-car-

boxypropyldisulfide, trigonal bipyramidal geometry is

observed (Lebl et al., 1996). The antifungal activity of all

the studied complexes revealed that the activity increases

on complexation, and the triorganotin complexes are

found to be more active than diorganotin complexes. UV

spectroscopic studies for the complexes 4 – 6 further show

the nonparticipation of the hetero atoms (other than the

coordinating atoms) present in the ligands in bonding to

the central tin metal ion.

Table 5 Antifungal activity for organotin(IV) complexes of ofloxacin.

Sr. no.

Solvent/complex

Average % inhibition after 24 h

C. albicans

Conc. (0.80 mg/ml)

Conc. (0.40 mg/ml)

I CHCl 3 / n -Bu 2 Sn(L 2 ) 2 7.5 43.9 II CHCl 3 / n -octyl 2 Sn(L 2 ) 2 7.4 41.2 III CHCl 3 / n -Bu 3 Sn(L 2 ) 2 12.5 62.4




Experimental

Materials All the di- and triorganotin(IV) compounds were purchased from

Alpha products (Sigma-Aldrich, New Delhi, India) and were used as

such. All the reactions were carried out under anhydrous conditions.

The solvents used were dried before use according to the literature

method (Armarego and Chai, 2003).

Instruments and measurements Melting points were determined in a capillary tube on an electro-

thermal melting point apparatus. UV spectra for the complexes were

recorded at 250 – 500 nm with a Systronics Double beam spectropho-

tometer 2203. IR spectra for the complexes ( 1 – 9 ) were recorded on a

PerkinElmer FTIR spectrophotometer at 4000 – 200 cm -1 . The 1 H NMR,

13 C and 119 Sn NMR were recorded on a Bruker Avance II 400 NMR

spectrometer. All chemical shift values were reported with respect to

tetramethylsilane as internal solvent. Carbon, hydrogen and nitrogen

(CHN) analysis of the samples was performed on the PerkinElmer

model 2400 CHN Analyzer.

Synthesis of dibutyltin, dioctyltin and bis(tributyltinoxide) complexes of albendazole, ofloxacin and 3-carboxypropyldisulfide Dialkyl/trialkyltin(IV) oxide (1 mmol) and the ligands (L 1 H, L 2 H) (2

mmol) and (L 3 H 2 ) (1 mmol) were dissolved in a mixture of dry ben-

zene (30 ml) and methanol (L 1 H, L 2 H, L 3 H 2 ) (10 ml). The reaction mix-

ture was then heated at refl ux and the water was removed by azeo-

tropic distillation. The dialkyl/trialkyltin(IV) oxide dissolved within

10 – 15 min to give a clear solution. Refl uxing was further continued

for 3 – 4 h and the contents were fi ltered and then cooled. Excess sol-

vent was removed by distillation, leaving behind a solid complex.

All the solids were recrystallized from the mixture of methanol and

hexane (5:1) and dried in vacuo at 40 – 50 ° C for 2 – 3 h. Purity of the

complexes was checked by thin-layer chromatography using silica

gel-G as adsorbent.

Antifungal activity The biological activity for the synthesized complexes was studied on

C. albicans , a representative model organism used to screen the anti-

fungal activity. The organism was procured from the Microbial Type

Culture Collection Centre, Institute of Microbial Technology, Chan-

digarh, India. To study the eff ects of newly synthesized complexes,

these were dissolved in dimethyl sulfoxide/chloroform/methanol/

ethanol and dichloromethane and kept at 4 ° C until further use.

The organism was cultured in Sabouraud dextrose broth medium at

30 ° C and then subcultured aft er every 36 h so as to maintain it in log

phase. For all the experiments, actively proliferating log phase cells

were taken, and the antifungal activities of various complexes were

studied by growing the cells at the fi nal concentrations of 0.80 and

0.40 mg/ml in a total of 2 ml of culture medium. Cells of C. albicans

were counted with a hemocytometer, and 1 × 10 5 cells per milliliter of

the medium were used as inoculum. Growth of cells was measured by

optical density measurement at 600 nm. Experiments were conducted

with the yeast form of C. albicans grown at 30 ° C in the presence of the

above complexes at the fi nal concentrations of 0.80 and 0.40 mg/ml.

Cell turbidity was measured aft er 24 h at 600 nm.

Acknowledgments: We are thankful to the Department of

Applied Sciences, PEC University of Technology, Chandi-

garh, India, for financial support. We are also grateful to

the head of the chemistry department, Panjab University,

and the University Institute of Engineering and Technol-

ogy, Chandigarh, for providing instrumental facilities for

product analysis. Dr. J. K. Puri, former professor and head

of inorganic chemistry, Punjab University, is thankful to

the University Grant Commission for the award of Emeritus

Professor Fellow 2010 in order to continue his research.

Received November 15, 2011; accepted January 22, 2013

References Affan, M. A.; Fasihuddin, B. A.; Liew, Y. Z.; Foo, S. W.; Ismail, J.

Synthesis, spectroscopic characterization and antibacterial activity of organotin(IV) complexes containing hydrazone ligand: X-ray single crystal structure of [ n -Bu 2 Sn(H 2 PAI) ‧ H 2 O]. J. Sci. Res. 2009 , 1 , 306 – 316.

Armarego, W. L. F.; Chai, C. L. L. Purification of laboratory chemicals . 5 th Edition. Butterworth-Heinemann: London, 2003.

Bonire, J. J.; Fricker, S. P. The in vitro antitumor profile of some 1,2-diaminocyclohexane organotin complexes. J. Inorg. Biochem. 2001 , 83 , 217 – 221.

Casas, J. S.; Castineiras, A.; Condori, F.; Couce, M. D.; Russo, U.; Sanchez, A.; Sordo, J.; Varela, J. M. Reaction of the

diethyltin(IV) cation with pyridoxine (PN, vitamin B 6 ) in the presence of various anionic species: the crystal structure of [SnEt 2 (PN-H)]Cl. Polyhedron 2000 , 19 , 813 – 819.

Choudhary, M. A.; Mazhar, M.; Ali, S.; Song X.; Eng, G. Synthesis, characterization and biological activity of dimethyltin dicarbo-xylates containing germanium. Met.-Based Drugs 2002 , 8 , 275 – 281.

Dakternieks, D.; Jurkschat, K.; Dreumel, S. V.; Tiekink, E. R. T. Molecular dynamics within diorganotin systems: solution and solid state studies of new mixed distannoxane dimers [ t Bu 2 (Cl)SnOSn(Cl)R 2 ] 2 . Inorg. Chem. 1997 , 36 , 2023 – 2029.

Danish, M.; Ali, S.; Mazhar, M.; Badshah, A.; Tieknik, E. R. T. Crystal and molecular structures of bis[3-(2-furanyl)-2-propenoato)




di-n-butyltin] oxide and triphenyltin 3-(2-furanyl)-2-propenoate. Main Group Met. Chem. 1995 , 18 , 697 – 706.

El-Metwaly, N. M.; Refat, M. S. Spectral, thermal, kinetic, molecular modeling and eukaryotic DNA degradation studies for a new series of albendazole (HABZ) complexes. Spectrochim. Acta Part A 2011 , 78 , 196 – 204.

Holecek, J.; Nadvorn ı k, M.; Handl ı r, K.; Lycka, A. 13 C and 119 Sn NMR spectra of di-n-butyltin(IV) compounds. J. Organomet. Chem. 1986 , 315 , 299 – 308.

Holmes, R. R.; Schmid, C. G.; Chandrasekhar, V.; Day, R. O.; Homels, J. M. Oxo carboxylate tin ladder clusters. A new structural class of organotin compounds. J. Am. Chem. Soc. 1987 , 109 , 1408 – 1414.

Jain, V. K. Mono-, bi- and high-nuclearity organotin complexes. Proc. Indian Acad. Sci., Chem. Sci. 1996 , 108 , 165 – 174.

Lebl, T.; Holecek, J.; Lycka, A. Coordinating behavior of carboxylic group. Sci. Pap. Univ. Pardubice, Ser. A 1996 , 2 , 5 – 24.

Malhotra, R.; Mehta, J.; Puri, J. K. Heterobimetallic complexes containing iron (II) and hexa-coordinated organosilicon. Cent. Eur. J. Chem. 2007 , 5 , 858 – 867.

Narula, S. P.; Meenu, Anand, R. D.; Puri, J. K.; Shankar, R. Synthesis and characterization of pentacoordinate silicate anions with six membered rings. Main Group Met. Chem. 2000a , 23 , 405 – 408.

Narula, S. P.; Shankar, R.; Puri, M.; Puri, J. K. Preparation and characterization of alkaline earth metal salts of bis(benzene-1,2-diolato)diisothiocyanatosilicate. Phosphorus, Sulfur Silicon Relat. Elem. 2000b , 158 , 1 – 7.

Narula, S. P.; Puri, J. K.; Puri, M. Synthesis and characterization of bis(maleato) diisothiocyanato silicates. New hexa coordinated silicate dianions with seven membered rings. Main Group Met. Chem. 2002a , 25 , 655 – 658.

Narula, S. P.; Soni, S.; Malhotra, R.; Meenu, Puri, J. K. 1,1,1-Tetrakis-( o -fluorophenylamino)silane tris [titanium(IV) chloride]. Evidence for new titanium cation [Ti 2 Cl 2 ] + 2 . Trans. Met. Chem. 2002b , 27 , 795 – 798.

Narula, S. P.; Puri, M.; Garg, N.; Puri, J. K.; Chadha, R. K. Discrete spirobicyclic silicate anions with SiO 2 N 2 C, SiN 2 S 2 C and SiO 4 C frameworks. Phosphorus, Sulfur Silicon Relat. Elem. 2007 , 182 , 569 – 587.

Nath, M.; Yadav, R; Eng, G.; Nguyen, T. T.; Kumar, A. Characteristic spectral studies, and antimicrobial and anti-inflammatory activities of diorganotin(IV) derivatives of dipeptides. J. Organomet. Chem. 1999 , 577 , 1 – 8.

Nath, M.; Pokharia, S.; Eng, G.; Song, X.; Kumar, A. Comparative study of structure-activity relationship of di- and tri-organotin(IV) derivatives of amino acid and peptides. J. Organomet. Chem. 2003 , 669 , 109 – 123.

Nath, M.; Pokharia, S.; Eng, G.; Song, X.; Kumar, A. Diorganotin(IV) derivatives of dipeptides containing at least one essential amino acid residue: synthesis, characteristic spectral data, cardiovascular, and anti ‐ inflammatory activities. Synth. React. Inorg. Met. Org. Chem. 2004a , 34 , 1689 – 1708.

Nath, M.; Pokharia, S.; Eng, G.; Song, X.; Kumar, A.; Gielen, M.; Willem, R.; Biesemans, M. New trimethyltin(IV) derivatives of dipeptides: synthesis, characteristic spectral studies and biological activity. Appl. Organomet. Chem. 2004b , 18 , 460 – 470.

Nath, M.; Pokharia, S.; Eng, G.; Song, X.; Kumar, A. New triorganotin (IV) derivatives of dipeptides as models for metal – protein

interactions: synthesis, structural characterization and biological studies. Spectrochim. Acta Part A 2006 , 63 , 66 – 75.

Puri, J. K.; Kaur, H. Synthesis of macrocyclic compounds using diorganotin (IV) dicarboxylate as covalent templates. Orient. J. Chem. 2005 , 21 , 207 – 212.

Puri, J. K.; Singh, G.; Duggal, P. Synthesis and characterization of bis(2-aminobenzoato)diphenylsilicate and bis(2-aminothio-phenoxy)diphenylsilicate. New hexacoordinated silicate dianions with seven membered rings. Main Group Met. Chem. 2007 , 30 , 31 – 36.

Puri, J. K.; Kaur, H.; Singla, A. Synthesis of macrocyclic compounds of tin templates. Main Group Met. Chem. 2008a , 31 , 243 – 252.

Puri, J. K.; Singh, G.; Duggal, P. Synthesis, characterization and reactivity of a novel six-membered 1-isothiocyanato silatrane. Phosphorus, Sulfur Silicon Relat. Elem. 2008b , 183 , 1853 – 1861.

Puri, J. K.; Singh, R.; Chahal, V. K.; Sharma, R. P. Novel hexaco-ordinate organosilicon(IV) complexes of diethylenetriamine Schiff base with SiO 2 N 3 skeleton. ARKIVOC (Gainesville, FL, U. S.) 2009a , 11 , 247 – 256.

Puri, J. K.; Singh, R.; Kaur, V.; Singh, G.; Sharma, R. P. Synthesis and characterization of penta and hexa coordinated silicon compounds with Schiffs bases containing -NCS functionality. Main Group Met. Chem. 2009b , 32 , 79 – 83.

Puri, J. K.; Singh, R.; Chahal, V. K. Silatranes: a review on their synthesis, structure, reactivity and applications. Chem. Soc. Rev. 2011a , 40 , 1791 – 1840.

Puri, J. K.; Singh, R.; Chahal, V. K.; Sharma, R. P.; Wagler, J.; Kroke, E. New silatranes possessing urea functionality: synthesis, characterization and their structural aspects. J. Organomet. Chem. 2011b , 696 , 1341 – 1348.

Rosenberg, B.; Vancamp, L.; Krigas, T. Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode. Nature 1965 , 205 , 698 – 699.

Rosenberg, B.; VanCamp, L.; Trosko, J. E.; Mansour, V. H. Platinum compounds: a new class of potent antitumor agents. Nature 1969 , 222 , 385 – 386.

Sagdinc, S.; Bayar ı , S. Spectroscopic studies on the interaction of ofloxacin with metals. J. Mol. Struct. 2004 , 691 , 107 – 113.

Sandhu, G. K.; Hundal, R. Structural chemistry of organotin carboxylates: XIV. Diorganotin(IV) complexes of monochloroacetyl- l phenylalanine. Crystal structure of [ n Bu 2 Sn(O 2 C(CH 2 Ph)C(H)N(H)C(O)CH 2 Cl 2 ) 2 ]. J. Organomet. Chem. 1991 , 412 , 31 – 38.

Sandhu, G. K.; Kaur, H. Preparation and characterization of diorganolead (IV) and triorganolead (IV) derivatives of some aromatic carboxylic acids. Main Group Met. Chem. 1991 , 19 , 219 – 223.

Sandhu, G. K.; Kaur, H. Diphenyllead(IV) and triphenyllead(IV) complexes with some N-protected amino acids. Main Group Met. Chem. 1990a , 13 , 29 – 36.

Sandhu, G. K.; Kaur, H. Preparation and characterization of diphenyllead(IV) and triphenyllead(IV) complexes with N -protected amino-acids and the dipeptides. Appl. Organomet. Chem. 1990b , 4, 345 – 352.

Shah, F. A.; Shahzadi, S.; Ali, S.; Molloy, K. C.; Ahmad, S. Organotin(IV) complexes of 4,5 dimethoxy-2-nitrobenzoic acid: synthesis, characterization, and biological activity. Russ. J. Coord. Chem. 2009 , 35 , 896 – 902.




Shahzadi, S.; Ali, S. Structural chemistry of organotin (IV) complexes. J. Iran. Chem. Soc. 2008 , 5 , 16 – 28.

Shahzadi, S.; Shahid, K.; Ali, S.; Mazhar, M.; Badshah, A.; Ahmed, E.; Malik, A. Non-steroidal anti-inflammatory drugs (NSAIDs) as donor ligands in organotin(IV) derivatives: synthesis, spectroscopic characterization and biological applications. Turk. J. Chem. 2005 , 29 , 273 – 287.

Shahzadi, S.; Shahid, K.; Ali, S. coordination behavior of the carboxylate group in organotin(IV) derivatives of 2-[(2 ′ ,4 ′ ,6 ′ -tribromophenylamido)]benzoic acid and 3-[(2 ′ ,4 ′ ,6 ′ -tribromophenylamido)]propenoic acid: spectroscopic studies. Russ. J. Coord. Chem. 2007 , 33 , 403 – 411.

Shahzadi, S.; Shahid, K.; Ali, S.; Bakhtiar, M. Characterization and antimicrobial activity of organotin(IV) complexes of 2-[(2 ′ ,6 ′ -diethylphenylamido)]benzoates and 3-[(2 ′ ,6 ′ -diethyl-phenylamido)]propanoates . Turk. J. Chem . 2008 , 32 , 333 – 353.

Singh, R.; Puri, J. K.; Chahal, V. K.; Sharma, R. P.; Venugopalan, P. Synthesis and reactivity of novel 3-isothiocyanatopropyl-silatrane derived from aminopropylsilatranes: X ray crystal structure and theoretical studies. J. Organomet. Chem. 2010a , 695 , 183 – 188.

Singh, R.; Puri, J. K.; Sharma, R. P.; Malik, A. K.; Ferretti, V. Synthesis, characterization and structural aspects of 3-azidopropylsilatrane. J. Mol. Struct. 2010b , 982 , 107 – 112.

Storr, T.; Thompson, K. H.; Orvig, C. Design of targeting ligands in medicinal inorganic chemistry. Chem. Soc. Rev. 2006 , 35 , 534 – 544.

Ukita, T.; Nakamura, Y.; Kubo, A.; Yamamoto, Y.; Takahashi, Y.; Koetera, J.; Ikeo, T. 1-Arylnaphthalene lignan: a novel scaffold for type 5 phosphodiesterase inhibitor. J. Med. Chem. 1999 , 42 , 1293 – 1305.



Synthesis, spectroscopic and biological studies of diorganotin(IV) and triorganotin(IV) derivatives...

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