Supporting information

Synthesis, in vitro and in silico screening of ethyl 2-(6-substituted benzo[d]thiazol-2-ylamino)-2-oxoacetates as protein-tyrosine phosphatase 1B inhibitors§ Gabriel Navarrete-Vazquez a, *, Marleth Ramírez-Martínez a, Samuel Estrada-Soto a, Carlos Nava-Zuazo a, Paolo Paoli b, Guido Camici b, Jaime Escalante-García c, José L. Medina-Franco d, Fabian López-Vallejod, Rolffy Ortiz-Andrade e a Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Cuernavaca, Morelos, 62209 México.b Dipartimento di Scienze Biochimiche,Università degli Studi di Firenze, Firenze, 50134, Italy.c Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Cuernavaca, Morelos. 62209,

Méxicod Torrey Pines Institute for Molecular Studies, Port St. Lucie, FL 34987, USAeFacultad de Química, Universidad Autónoma de Yucatán, Mérida, Yucatán, 97000, México

*Corresponding author e-mail address: gabriel_navarrete@uaem.mx

Table of Contents

I. 1H NMR Spectrum of 2-(6-methylbenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–1). II. 13C NMR Spectrum of 2-(6-methylbenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–1). III. 1H NMR Spectrum of Ethyl 2-(benzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–2). IV. 13C NMR Spectrum of Ethyl 2-(benzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–2).V. 1H NMR Spectrum of Ethyl 2-(6-methoxybenzo[d]thiazol-2-ylamino)-2-oxoacetate

(OX–3). VI. 13C NMR Spectrum of Ethyl 2-(6-methoxybenzo[d]thiazol-2-ylamino)-2-oxoacetate

(OX–3). VII. 1H NMR Spectrum of Ethyl 2-(6-ethoxybenzo[d]thiazol-2-ylamino)-2-oxoacetate

(OX–4). VIII. 13C NMR Spectrum of Ethyl 2-(6-ethoxybenzo[d]thiazol-2-ylamino)-2-oxoacetate

(OX–4). IX. 1H NMR Spectrum of Ethyl 2-{6-(mehylsulfonyl)benzo[d]thiazol-2-ylamino}-2-

oxoacetate (OX–5).X. 13C NMR Spectrum of Ethyl 2-{6-(mehylsulfonyl)benzo[d]thiazol-2-ylamino}-2-

oxoacetate (OX–5).XI. 1H NMR Spectrum of Ethyl 2-(6-chlorobenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–

6).

XII. 13C NMR Spectrum of Ethyl 2-(6-chlorobenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–6).

XIII. 1H NMR Spectrum of Ethyl 2-(6-fluorobenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–7).

XIV. 13C NMR Spectrum of Ethyl 2-(6-fluorobenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–7).

XV. 1H NMR Spectrum of Ethyl 2-(6-nitrobenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–8).

XVI. 13C NMR Spectrum of Ethyl 2-(6-nitrobenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–8).

XVII. 1H NMR Spectrum of Ethyl 2-(6-aminobenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–9)

XVIII. 13C NMR Spectrum of Ethyl 2-(6-aminobenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–9)

I. 1H NMR Spectrum of 2-(6-methylbenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–1).

II. 13C NMR Spectrum of 2-(6-methylbenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–1).

III. 1H NMR Spectrum of Ethyl 2-(benzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–2).

IV. 13C NMR Spectrum of Ethyl 2-(benzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–2).

V. 1H NMR Spectrum of Ethyl 2-(6-methoxybenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–3).

VI. 13C NMR Spectrum of Ethyl 2-(6-methoxybenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–3).

VII. 1H NMR Spectrum of Ethyl 2-(6-ethoxybenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–4).

0.9982.167 2.0203.211 3.036PPM8.07.67.26.86.46.05.65.24.84.44.03.63.22.82.42.01.61.20.80.40.0

SpinWorks 3: MRM-11

file: ...\espectros_Mérida_yus\MRM-11\1\fid expt: <zg30>transmitter freq.: 400.132471 MHztime domain size: 65536 pointswidth: 8250.83 Hz = 20.6202 ppm = 0.125898 Hz/ptnumber of scans: 16freq. of 0 ppm: 400.130003 MHzprocessed size: 32768 complex pointsLB: 0.000 GF: 0.0000Hz/cm: 147.149 ppm/cm: 0.36775

8.71078.02037.99897.99457.99097.97287.9690 4.36324.34574.32794.31013.2619 1.34511.32741.3096

VIII. 13C NMR Spectrum of Ethyl 2-(6-ethoxybenzo[d]thiazol-2-ylamino)-2-oxoacetate(OX–4).

XI. 1H NMR Spectrum of Ethyl 2-{6-(mehylsulfonyl)benzo[d]thiazol-2-ylamino}-2-oxoacetate (OX–5).

X. 13C NMR Spectrum of Ethyl 2-{6-(mehylsulfonyl)benzo[d]thiazol-2-ylamino}-2-oxoacetate (OX–5).

PPM150140130120110100908070605040302010 0

SpinWorks 3: MRM-11

file: ...\espectros_Mérida_yus\MRM-11\2\fid expt: <zgpg30>transmitter freq.: 100.622830 MHztime domain size: 65536 pointswidth: 24038.46 Hz = 238.8967 ppm = 0.366798 Hz/ptnumber of scans: 2048freq. of 0 ppm: 100.612812 MHzprocessed size: 32768 complex pointsLB: 0.000 GF: 0.0000Hz/cm: 674.068 ppm/cm: 6.69896

161.6356158.6722157.4515151.5683136.0881132.1383125.1041122.4255121.2791 62.917744.0387 13.7898

XI. 1H NMR Spectrum of Ethyl 2-(6-chlorobenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–6).

0.9980.9911.026 2.108 3.099PPM7.67.26.86.46.05.65.24.84.44.03.63.22.82.42.01.61.20.80.40.0

SpinWorks 3: MRM-13

file: ...\espectros_Mérida_yus\MRM-13\1\fid expt: <zg30>transmitter freq.: 400.132471 MHztime domain size: 65536 pointswidth: 8250.83 Hz = 20.6202 ppm = 0.125898 Hz/ptnumber of scans: 16freq. of 0 ppm: 400.130002 MHzprocessed size: 32768 complex pointsLB: 0.000 GF: 0.0000Hz/cm: 134.002 ppm/cm: 0.33489

7.94507.92997.92327.82767.81567.80537.79337.32797.3212 4.34704.32934.31154.2937 1.33491.31701.2992

XII. 13C NMR Spectrum of Ethyl 2-(6-chlorobenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–6).

XIII. 1H NMR Spectrum of Ethyl 2-(6-fluorobenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–7).

XIV. 13C NMR Spectrum of Ethyl 2-(6-fluorobenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–7).

PPM1501401301201101009080706050403020100

SpinWorks 3: MRM-13

file: ...\espectros_Mérida_yus\MRM-13\2\fid expt: <zgpg30>transmitter freq.: 100.622830 MHztime domain size: 65536 pointswidth: 24038.46 Hz = 238.8967 ppm = 0.366798 Hz/ptnumber of scans: 2048freq. of 0 ppm: 100.612812 MHzprocessed size: 32768 complex pointsLB: 0.000 GF: 0.0000Hz/cm: 699.231 ppm/cm: 6.94903

160.1876158.9322157.7952157.5444157.1358157.1276144.8439132.9379132.8240122.0990122.0085114.8133114.5675108.5265108.2571 62.7977 13.7707

XVI. 1H NMR Spectrum of Ethyl 2-(6-nitrobenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–8).

XVII.13C NMR Spectrum of Ethyl 2-(6-nitrobenzo[d]thiazol-2-ylamino)-2-oxoacetate (OX–8).