Discovery of 2-amino-heteroaryl-benzothiazole-6-anilides as potent p56lck inhibitors

Das, Jagabandhu; Moquin, Robert V.; Lin, James; Liu, Chunjian; Doweyko, Arthur M.; DeFex, Henry F.; Fang, Qiong; Pang, Suhong; Pitt, Sidney; Shen, Ding Ren; Schieven, Gary L.; Barrish, Joel C.; Wityak, John

doi:10.1016/s0960-894x(03)00511-0

Cited by 100 publications

(52 citation statements)

References 12 publications

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“…The mixture was stirred at room temperature for 5 h. After completion of the reaction (monitored by TLC), the mixture was diluted with ethyl acetate (20 ml), washed with water (20 ml) and the aqueous layer was then extracted with ethyl acetate (3 × 10 ml). The combined organic layer was dried over MgSO 4 and concentrated under vacuum. Further purification was carried out by column chromatography on silica gel eluting with ethyl acetate/petroleum ether.…”

Section: General Synthetic Procedures For Tandem Synthesis Of 2-substimentioning

confidence: 99%

Cerium‐catalyzed tandem synthesis of 2‐substituted benzothiazoles in PEG

Jin

Cheng

Chen

2011

Applied Organom Chemis

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An efficient and convenient condensation reaction of 2-aminothiophenol with aldehydes catalyzed by a catalytic amount of ceric ammonium nitrate in polyethylene glycol was investigated. As a result, a set of diverse 2-substituted benzothiazoles such as 2-phenylbenzothiazole as well as its p-Me, p-NO 2 , p-F, p-Cl, p-Br, o-OMe, p-OMe and 2-furyl, 2-pyridyl and styryl derivatives were obtained in good to excellent yields for 5 h at room temperature. Additionally, the catalyst system was recovered and reused several times without evident loss in activity.

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Section: General Synthetic Procedures For Tandem Synthesis Of 2-substimentioning

confidence: 99%

Cerium‐catalyzed tandem synthesis of 2‐substituted benzothiazoles in PEG

Jin

Cheng

Chen

2011

Applied Organom Chemis

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“…The 2-aminopyridyl analogue and 2-aminopyrimidinyl analogue (3.11) were identified as potent lck inhibitors with excellent cellular activities against T-cell proliferation 92 . Anti-inflammatory activity of O-substituted-4-benzothiazoles (3.12) was determined and most of the derivatives were found potent inhibitors of Bradykinin B 2 receptor.…”

Section: 8mentioning

confidence: 99%

Untitled

2011

IJPSR

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Recently, heterocyclic compounds analogues and their derivatives have attracted strong interest in medicinal chemistry due to their biological and pharmacological properties. The small and simple benzothiazole nucleus possesses numerous biological properties like -antitumor, antimicrobial, anti-inflammatory, anticonvulsant, and antidiabetic activities. These activities are also possessed by its substituted derivatives as well. The present review focuses on some commonly used easy procedures to synthesize the benzothiazole moiety and its derivatives, which comprise of different biological activities.

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“…Benzothiazoles exhibit a variety of biological properties including antifungal [11], anticancer [12,13], antiamyloid [14], and antirheumatic [15], and have attracted considerable attention. They have been widely used as important pharmacophores for exploration of novel and highly active antitumor compounds in medicinal chemistry (4-6, Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Benzothiazole Derivatives Bearing the ortho‐Hydroxy‐N‐acylhydrazone Moiety as Potent Antitumor Agents

Zhang

Han

et al. 2014

Archiv der Pharmazie

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A novel series of benzothiazole derivatives bearing the ortho-hydroxy-N-acylhydrazone moiety were designed, synthesized, and evaluated for their procaspase-3 kinase activation activities and antiproliferative activities against five cancer cell lines (NCI-H226, SK-N-SH, HT29, MKN-45, and MDA-MB-231). Most target compounds showed moderate to excellent cytotoxic activity against all five tested cancer lines. The most promising compound 18e (procaspase-3 EC50 = 0.31 µM) with IC50 values ranging from 0.24 to 0.92µM against all tested cell lines was 4.24-12.2 times more active than PAC-1 (procaspase-3 EC50 = 0.41 µM). Structure-activity relationship studies indicated that the phenyl group on the 2-hydroxyphenyl ring (moiety A) was critical for pharmacological activity in vitro. In addition, introduction of a benzyloxyl group on moiety A and a mono-electron-withdrawing group at the 4-position of the benzyloxyl group were more favorable for antitumor activity. Moreover, reduction of the electron density in the phenyl ring of the benzyloxy group led to a dramatic decrease in the procaspase-3 kinase activation activity.

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Discovery of 2-amino-heteroaryl-benzothiazole-6-anilides as potent p56lck inhibitors

Cited by 100 publications

References 12 publications

Cerium‐catalyzed tandem synthesis of 2‐substituted benzothiazoles in PEG

Cerium‐catalyzed tandem synthesis of 2‐substituted benzothiazoles in PEG

Untitled

Synthesis and Biological Evaluation of Benzothiazole Derivatives Bearing the ortho‐Hydroxy‐N‐acylhydrazone Moiety as Potent Antitumor Agents

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