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102337-98-4

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102337-98-4 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 102337-98-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,2,3,3 and 7 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 102337-98:
(8*1)+(7*0)+(6*2)+(5*3)+(4*3)+(3*7)+(2*9)+(1*8)=94
94 % 10 = 4
So 102337-98-4 is a valid CAS Registry Number.

102337-98-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name benzo[d]thiazol-2-amine

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:102337-98-4 SDS

102337-98-4Relevant articles and documents

Synthesis, anti-proliferative activity, SAR, and kinase inhibition studies of thiazol-2-yl- substituted sulfonamide derivatives

Pawar, Chandrakant D.,Chavan, Sadhana L.,Pawar, Umakant D.,Pansare, Dattatraya N.,Deshmukh, Santosh V.,Shinde, Devanand B.

, p. 257 - 264 (2019)

A series of novel thiazol-2-yl substituted-1-sulfonamide derivatives were synthesized from anilines. This involved the coupling of sulfonyl chlorides with thiazol amine to obtain the final compounds 7a–7j and 8a–8j. All synthesized compounds were screened for anticancer activity against MCF-7, HeLa, A-549, and Du-145 cancer cell lines by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Preliminary bioassay suggests that most of the compounds show anti-proliferation to different degrees, with doxorubicin used as positive control. The synthesized compounds show IC50 values in the range 2.74–8.17 μM in the different cell lines. The compounds 7d, 7e, 8a, 8d, and 8e were active compared to doxorubicin. The compounds having butyl and pantyl chains were more active than their lower and higher carbon chains and also their ring counterparts.

Multi-step synthesis, photophysical and physicochemical investigation of novel pyrazoline a heterocyclic D- π -A chromophore as a fluorescent chemosensor for the detection of Fe3+ metal ion

Khan, Salman A.

, (2020)

The title compound has been 2-(1-(benzo[d]thiazol-2-yl)-5-(3,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenol (BTDP) synthesized by reaction of (E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (DMPO) with 2-Hydrazinylbenzo[d]thiazole. DMPO was synthesized by the reaction of 1-(2 hydroxyphenyl)ethan-1-one with 3,4-dimethoxybenzaldehyde. Structure of compound has been confirmed by the elemental analysis and spectroscopic techniques (FT-IR, 1H NMR and 13C NMR). Photophysical properties of the BTDP such as absorption, emission, stokes shift, transition dipole moments and fluorescence quantum yield have been studied in various solvents of different polarity and chromophore demonstrated positive solvatochromism. The chromophore undergoes micellization in two different micelles and its can be used as probe to determine the critical micelle concentration of surfactant such as CTAB and SDS. In addition, Pyrazoline derivative used as fluorescent chemosensor for metal ion selectively based on fluorometric detraction and pyrazoline displayed as on-off fluorescence chemosensor for the determination of Fe3+ ion in solution. Hildebrand, Stern-Volmer and job's plot method has described quenching behavior of chromophore with Fe3+ ion.

Synthesis and Antibacterial Activity of Sulfur-linked Bis and Tris Heterocycles

Mallikarjuna Reddy,Lavanya,Lakshmi Teja,Padmaja,Padmavathi

, p. 2755 - 2766 (2017)

The bis and tris heterocycles-benzoxazolyl/benzothiazolyl/benzimidazolyl quinazolines linked by sulfur and/or nitrogen were prepared from 2,4-dichloroquinazoline and benzazolyl-2-thiol/benzazolyl-2-amine and studied their antibacterial activity. The nitro-substituted sulfur-linked bisbenzothiazolylquinazoline (12f), bisbenzimidazolylquinazoline (13f), and nitro-substituted sulfur and nitrogen-linked bisbenzothiazolylquinazoline (15f) were found to be potential antibacterial agents against Staphylococcus aureus.

-

Fujiki et al.

, p. 614 (1979)

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Formation of nitrogen-containing heterocycles using di(imidazole-1-yl)methanimine

Wu, Yong-Qian,Limburg, David C.,Wilkinson, Douglas E.,Hamilton, Gregory S.

, p. 191 - 193 (2003)

A mild and efficient synthesis of five- and six-membered nitrogen containing heterocyclic compounds, in which di(imidazole-1-yl)methanimine serves as a one-carbon source, is reported.

Synthesis and molecular docking of new roflumilast analogues as preferential-selective potent PDE-4B inhibitors with improved pharmacokinetic profile

Moussa, Bahia A.,El-Zaher, Asmaa A.,El-Ashrey, Mohamed K.,Fouad, Marwa A.

, p. 477 - 486 (2018)

In the present work, we designed and synthesized new roflumilast analogues with preferential-selective PDE-4B inhibition activity and improved pharmacokinetic properties. The unsubstituted benzo[d]thiazol-2-yl and -6-yl benzamide derivatives (4a and 6a) showed both good potency and preferential selectivity for PDE-4B. More remarkably, 6c revealed 6 times preferential PDE-4B/4D selectivity with a significant increase of in vitro cAMP and good % inhibition of TNF-α concentration. In addition, the in vitro pharmacokinetics of 6c showed good metabolic stability with in vitro CLint (5.67 mL/min/kg) and moderate % plasma protein binding (53.71%). This was reflected onto increased in vivo exposure with a half-life greater than roflumilast by 3 folds (21 h) and a Cmax value of 113.958 ng/mL. Molecular docking attributed its good activity to its key binding interactions in PDE-4B active site with additional hydrogen bonding with amino acids lining the metal pocket. Summing up, 6c can be considered as suitable candidate for further investigation for the treatment of COPD.

Synthesis, Type II diabetes inhibitory activity, antimicrobial evaluation and docking studies of indeno[1,2-c]pyrazol-4(1H)-ones

Mor, Satbir,Sindhu, Suchita

, p. 46 - 62 (2020)

We report a convenient and efficient synthesis of indeno[1,2-c]pyrazol-4(1H)-ones (4a?o) by the reaction of a variety of 2-acyl-(1H)-indene-1,3(2H)-diones (1) and 2-hydrazinylbenzo[d]thiazole/2-hydrazinyl-6-substitutedbenzo[d]thiazoles (2) in the presence of glacial acetic acid in good yields. The structure of the compounds thus prepared were confirmed by analytical and spectral (FT-IR, 1H NMR, 13C NMR, and HRMS) techniques. All the synthesized indeno[1,2-c]pyrazol-4(1H)-ones (4a?o) were assayed for their in vitro Type II diabetes inhibitory activity by using Acarbose as standard drug and in vitro antimicrobial activity utilizing Streptomycin and Fluconazole as reference drugs. Among the synthesized derivatives, 4e (IC50 = 6.71 μg/mL) was found to be more potent against α-glucosidase enzyme as compared with the standard Acarbose (IC50 = 9.35 μg/mL) and 4i (IC50 = 11.90 μg/mL) exhibited good inhibitory activity against α-amylase enzyme as compared with the standard Acarbose (IC50 = 22.87 μg/mL). Also, all the titled compounds showed good antimicrobial activity. In addition, in vitro α-glucosidase and α-amylase inhibition were supported by docking studies performed on the derivatives 4e and 4o, respectively. [Figure not available: see fulltext.].

Design and synthesis of new derivatives of 3H-quinazolin-4-one as potential anticonvulsant agents

Kabra, Uma,Chopde, Chandrabhan,Wadodkar, Sudhir

, p. 1351 - 1355 (2011)

As a part of systematic investigation on synthesis and biological activities, some new derivatives of 2-ethyl-3-(substituted benzothiazole- 2′-yl)-[3H]-quinazolin-4-ones 3 have been synthesized, and the structures of the compounds were confirmed by elemental analysis and spectral data. The newly synthesized derivatives are then screened for anticonvulsant activity by maximal electroshock method. Copyright

Discovery of 18β-glycyrrhetinic acid conjugated aminobenzothiazole derivatives as Hsp90-Cdc37 interaction disruptors that inhibit cell migration and reverse drug resistance

Jin, Le,Huang, Rizhen,Huang, Xiaochao,Zhang, Bin,Ji, Min,Wang, Hengshan

, p. 1759 - 1775 (2018)

A series of 18β-glycyrrhetinic acid (GA) conjugated aminobenzothiazole derivatives were designed, synthesized and evaluated for disruption activity of Hsp90-Cdc37 as well as the effects of in vitro cell migration. These compounds exhibited relatively good disruption activity against Hsp90-Cdc37 with IC50 values in low micromolar range. A docking study of the most active compound 11g revealed key interactions between 11g and Hsp90-Cdc37 complex in which the benzothiazole moiety and the amine chain group were important for improving activity. It is noteworthy that further antitumor activity screening revealed that some compounds exhibited better inhibitory activity than the commercial anticancer drug 5-FU and showed potent suppression activity against drug-resistant cancer cells. In particular, compound 11 g appeared to be the most potent compound against the A549 cell line, at least partly, by inhibition of the activity of Hsp90 and apoptosis induction. The treatment of A549 cells with compound 11g resulted in inhibition of in vitro cell migration through wound healing assay and S phase of cell cycle arrested. In addition, 11g-induced apoptosis was significantly facilitated in A549 cells. Thus, we conclude that GA aminobenzothiazole derivatives may be the potential Hsp90-Cdc37 disruptors with the ability to suppress cells migration and reversed drug-resistant.

Multi-Step Synthesis, Physicochemical investigation and optical properties of pyrazoline derivative: A Donor-π-Acceptor chromophore

Alfaifi, S. Y.,Alimuddin,Almalki, Abdulraheem S. A.,Alsharif, Meshari A.,Khan, Salman A.,Kumar, Sanjay,Obaid, Rami J.,Syed, Salauddin,Ullah, Qasim

, (2021)

The new extended π-bond pyrazoline derivative (ENTD) was prepared from heterocyclic chalcone with 2-hydrazinylbenzo[d] thiazole. The spectroscopic methods established the structure of the ENTD, and the elemental analysis established the purity of the ENTD. In ten different solvents, physicochemical ENTD parameters such as the molar absorption coefficient, transition dipole moments, Stokes shift, oscillator intensity and fluorescence quantum yield were determined to see the effect of the solvent with pyrazoline derivative (ENTD) on the basis of different polarity. In addition, the interaction of ENTD chromophore with the cationic and anionic surfactants have been studied. The intensity of fluorescence spectrum of the ENTD was found to increase with an increase in the surfactant concentration. This indicates that there is a strong interaction between ENTD and surfactants. The ENTD chromophore can therefore be used as a probe to define the surfactants' CMC.

-

Lemons et al.

, p. 1953 (1941)

-

Synthesis and antimicrobial activity of amino linked heterocycles

Mallikarjuna Reddy, Lingaladinne,Dinneswara Reddy, Guda,Padmaja, Adivireddy,Padmavathi, Venkatapuram

, p. 75 - 80 (2015)

Amino-linked benzoxazolyl/benzothiazolyl/benzimidazolyl quinazolines were prepared and their antimicrobial activity studied. The nitro-substituted benzothiazolyl quinazoline (8f) may be a potential antibacterial agent against Staphylococcus aureus and nitro-substituted benzimidazolyl quinazoline (9f) may be a potential antifungal agent against Aspergillus niger.

-

Sycheva,T.P. et al.

, (1970)

-

Synthesis, characterization and studies on antioxidant and molecular docking of metal complexes of 1-(benzo[d]thiazol-2-yl)thiourea

Yapati, Harinath,Devineni, Subba Rao,Chirumamilla, Suresh,Kalluru, Seshaiah

, p. 43 - 51 (2016)

In the present study, a new thiourea derivative bearing benzothiazole ligand, 1-(benzo[d]thiazol-2-yl)thiourea (btt) and its ternary metal (Cu(II), Co(II) and Ni(II)) complexes were synthesized. The structural characterization was carried out by micro analysis, IR, 1H-NMR, EPR, UV-Visible spectral analyses, molar conductance and thermal analysis studies. Spectral studies of complexes revealed that the metal complexes have distorted octahedral geometry. Molecular modelling study was performed to evaluate the recognition of target compounds at the 3MNG binding pocket. The docking results revealed that copper complex selectively binds to the crucial amino acid residues in the active site of 3MNG. The in vitro antioxidant activity of the ligand and its metal complexes was assayed by radical scavenging activity (DPPH, H2O2 and NO) and ferric reducing antioxidant power (FRAP) methods. The ligand showed moderate antioxidant activity whereas the metal complexes exhibited better antioxidant activity than that of the ligand. The results of the four methods proved that the copper complex is the most potent antioxidant among all the tested compounds.

Cross-coupling of aryl/heteroaryl bromides with ammonia using a copper-carbene catalyst

Ntaganda, Rukundo,Dhudshia, Bhartesh,Macdonald, Charles L. B.,Thadani, Avinash N.

, p. 6200 - 6202 (2008)

A variety of aryl and heteroaryl bromides were cross-coupled with ammonia in good to high yields in the presence of a copper-NHC catalyst. The Royal Society of Chemistry.

Design, synthesis and biological evaluation of benzimidazolyl and benzothiazolyl picolinamide derivatives as antimicrobial agents

Namani, Vasu,Bharath Kumar Goud,Bharathi Kumari,Kumbham, Ramesh,Balakrishna, Kannoju,Bhima, Bhukya

, p. 4575 - 4578 (2015)

A series of benzothiazolyl amides and benzimidazolyl amides (6a-f) has been synthesized from the coupling reaction of substituted picolinic acid with benzothiazole and benzimidazoles, respectively. The newly synthesized compounds were evaluated for their efficacy as antimicrobial agents against various Gram-positive and Gram-negative strains of bacteria and fungal strains. Amongst these compounds 6f was found to be the most potent against Bacillus subtilis and Candida albicans. Moreover, other compounds also found to be potential antibacterial agents in comparison to the standard drugs.

A NOVEL SYNTHESIS OF 2-BENZOTHIAZOLAMINE AND ITS DERIVATIVES BY A NICKEL(0)-CATALYZED REACTION OF 1,2-AMINOIODOARENES WITH THIOUREAS

Takagi, Kentaro

, p. 265 - 266 (1986)

In the presence of a nickel(0) complex, 1,2-aminoiodoarenes underwent the reaction with thioureas to provide a facile, site-specific, and general synthetic procedure of 2-benzothiazolamine and its derivatives under non-oxidative conditions.

Access to a new class of biologically active quinoline based 1,2,4-triazoles

Patel, Rahul V.,Park, Se Won

, p. 24 - 30 (2014)

As an aspect of our ongoing research in search of new antimicrobial armamentarium, a series of 1,2,4-triazol-3-ylthio-acetamides was constructed and in vitro analyzed for their antimicrobial activity against several bacteria and fungi. Aiming to establish an increased potency, the bioassay results were matched to those of 1,3,4-oxadiazoles, utilized previously. Remarkably, 1,2,4-triazoles were found to possess a good spectrum of antifungal potency, which eventually suggested the azole template as an essential pharmacophore to diversify the biological occupations of the attendant molecules. However, it was noticed that the potency of final analogs against each strain placed reliance on the type of substituent present on benzothiazole ring. The structures of final compounds were confirmed with the aid of IR, 1H NMR, 13C NMR spectroscopy and CHN analysis.

Development of selective DprE1 inhibitors: Design, synthesis, crystal structure and antitubercular activity of benzothiazolylpyrimidine-5-carboxamides

Chikhale, Rupesh,Menghani, Sunil,Babu, Ramavath,Bansode, Ratnadeep,Bhargavi,Karodia, Nazira,Rajasekharan,Paradkar, Anant,Khedekar, Pramod

, p. 30 - 46 (2015)

Decaprenylphosphoryl-b-d-ribose 20-epimerase (DprE1) is a potential drug target for development of antitubercular agents. Structure based drug discovery approach yielded twenty novel derivatives of benzothiazolylpyrimidine-5-carboxamides (7a-t) which were synthesised by three component one pot reaction involving benzothiazolyl oxobutanamide, thiourea and substituted aromatic benzaldehydes. These derivatives were evaluated for antitubercular activity to determine MIC and compound 7a, 7e, 7f and 7o were found to be potentially active against Mycobacterium tuberculosis (H37Rv). Log P of these compounds was found to be between 2.0 and 3.0 making them suitable for oral dosing. DprE1 selectivity and pharmacokinetic studies were carried out for these compounds of which 7a and 7o were found to be highly selective and bioavailability was found to be above 52% by oral dose. Crystal structure of 7a was studied and molecular packing was determined, it exhibited a triclinic crystal lattice arrangement having hydrogen bonded dimeric arrangement. Drug receptor interactions were studied which exhibited docking in the active site of receptor with hydrogen bonding, hydrophobic interactions, vdW interactions with amino acid residues such as Cys387, Asn385, Lys418, Tyr314, Gln334 and Lys367 respectively. 3D QSAR analysis was carried out by kNN-MFA method to determine and develop theoretical model, best suitable model was found to be based on Simulated Annealing k-Neariest Neighbour Molecular Field Analysis (SA kNN-MFA). The model provided with hydrophobic descriptors in positive side indicating the need of bulky groups, steric and electronegative descriptors in negative coordinates hints with contribution by the electronegative substitutions as favourable and desirable moieties for enhancing the activity. The q2, q2-se and Pred-r2se were found to be 0.5000, 0.6404 and 1.0094 respectively. A pharmacophore model was generated which suggested for necessity of aromatic, aliphatic carbon centre and hydrogen bond donor for development of newer DprE1 selective inhibitors.

-

Kost et al.

, (1978)

-

Scalable synthesis and antibacterial evaluation of 2-(3-(N-(substituted phenyl)sulfamoyl)ureido)benzothiazoles

Cheraiet, Zinelaabidine,Meliani, Saida,Nessaib, Mounir,Hessainia, Sihem,Boukhari, Abbas,Djahoudi, Abdelghani,Regainia, Zine

, (2019)

A new series of 2-(3-(N-(substituted phenyl)sulfamoyl)ureido)benzothiazoles was synthesized via a one-pot efficient and scalable method, involving the condensation of 2-aminobenzothiazoles derivatives, substituted anilines, and chlorosulfonyl isocyanate. The products were obtained in good yield with a simple workup, and their structures were confirmed from their spectral analyses. The synthesized compounds were further screened for their antibacterial activity against Gram-positive and Gram-negative pathogenic strains. The molecules show promising activity in the MIC value range of 2–0.25 μg/ml against selected bacterial strains, especially against nonfermentative carbapenem-resistant bacteria (Pseudo VIM-2 and Acinetobacter baumanni).

Chemical Genetics Reveals a Role of Squalene Synthase in TGFβ Signaling and Cardiomyogenesis

Takemoto, Yasushi,Kadota, Shin,Minami, Itsunari,Otsuka, Shinya,Okuda, Satoshi,Abo, Masahiro,Punzalan, Louvy Lynn,Shen, Yan,Shiba, Yuji,Uesugi, Motonari

supporting information, p. 21824 - 21831 (2021/08/30)

KY02111 is a widely used small molecule that boosts cardiomyogenesis of the mesoderm cells derived from pluripotent stem cells, yet its molecular mechanism of action remains elusive. The present study resolves the initially perplexing effects of KY02111 on Wnt signaling and subsequently identifies squalene synthase (SQS) as a molecular target of KY02111 and its optimized version, KY-I. By disrupting the interaction of SQS with cardiac ER-membrane protein TMEM43, KY02111 impairs TGFβ signaling, but not Wnt signaling, and thereby recapitulates the clinical mutation of TMEM43 that causes arrhythmogenic right ventricular cardiomyopathy (ARVC), an inherited heart disease that involves a substitution of myocardium with fatty tissue. These findings reveal a heretofore undescribed role of SQS in TGFβ signaling and cardiomyogenesis. KY02111 may find its use in ARVC modeling as well as serve as a chemical tool for studying TGFβ/SMAD signaling.

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