Synthesis of 3‐substituted‐2‐benzothiazolinone, 2‐benzoxazolinone and benzothiazoline‐2‐thione

D'Amico, John J.; Bollinger, F. G.

doi:10.1002/jhet.5570260508

Cited by 9 publications

(2 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Alkylation of ( 5 ) to give the corresponding unreported N-alkylated intermediates ( 6a–b ) was attempted in KOH/acetone/water mixture using appropriate aralkyl halide under reflux conditions [25] to obtain the desired intermediates ( 6a–b ) in an excellent yield.…”

Section: Resultsmentioning

confidence: 99%

Applying Ligands Profiling Using Multiple Extended Electron Distribution Based Field Templates and Feature Trees Similarity Searching in the Discovery of New Generation of Urea-Based Antineoplastic Kinase Inhibitors

et al. 2012

View full text Add to dashboard Cite

This study provides a comprehensive computational procedure for the discovery of novel urea-based antineoplastic kinase inhibitors while focusing on diversification of both chemotype and selectivity pattern. It presents a systematic structural analysis of the different binding motifs of urea-based kinase inhibitors and the corresponding configurations of the kinase enzymes. The computational model depends on simultaneous application of two protocols. The first protocol applies multiple consecutive validated virtual screening filters including SMARTS, support vector-machine model (ROC = 0.98), Bayesian model (ROC = 0.86) and structure-based pharmacophore filters based on urea-based kinase inhibitors complexes retrieved from literature. This is followed by hits profiling against different extended electron distribution (XED) based field templates representing different kinase targets. The second protocol enables cancericidal activity verification by using the algorithm of feature trees (Ftrees) similarity searching against NCI database. Being a proof-of-concept study, this combined procedure was experimentally validated by its utilization in developing a novel series of urea-based derivatives of strong anticancer activity. This new series is based on 3-benzylbenzo[d]thiazol-2(3H)-one scaffold which has interesting chemical feasibility and wide diversification capability. Antineoplastic activity of this series was assayed in vitro against NCI 60 tumor-cell lines showing very strong inhibition of GI50 as low as 0.9 uM. Additionally, its mechanism was unleashed using KINEX™ protein kinase microarray-based small molecule inhibitor profiling platform and cell cycle analysis showing a peculiar selectivity pattern against Zap70, c-src, Mink1, csk and MeKK2 kinases. Interestingly, it showed activity on syk kinase confirming the recent studies finding of the high activity of diphenyl urea containing compounds against this kinase. Allover, the new series, which is based on a new kinase scaffold with interesting chemical diversification capabilities, showed that it exhibits its “emergent” properties by perturbing multiple unexplored kinase pathways.

show abstract

Section: Resultsmentioning

confidence: 99%

Applying Ligands Profiling Using Multiple Extended Electron Distribution Based Field Templates and Feature Trees Similarity Searching in the Discovery of New Generation of Urea-Based Antineoplastic Kinase Inhibitors

et al. 2012

View full text Add to dashboard Cite

show abstract

“…The first step in the synthetic sequence reacts 2-benzothiazolinone with 4-vinylbenzyl chloride under basic conditions using methods similar to that described by J. D'Amico et al to yield the N -styryl-substituted benzothiazolinone ( 1 ) as a white crystalline solid in 91−93% yield …”

mentioning

confidence: 99%

Two Polymerizable Derivatives of 2,2‘-Azino-bis(3-ethylbenzthiazoline-6-sulfonic acid)

et al. 2005

View full text Add to dashboard Cite

[structure: see text] A versatile strategy for the synthesis of polymerizable derivatives of the redox-active indicator dye 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) is reported. Two products are shown to illustrate how the final step in the synthetic strategy can be used to alter the physical properties of the product. Both products were characterized spectroscopically and electrochemically. The hydrophilic monomer (sABTS) was polymerized, and the utility of this polymer (polyABTS) is demonstrated in the context of bioelectrocatalysis.

show abstract

ChemInform Abstract: Synthesis of 3‐Substituted‐2‐benzothiazolinone, 2‐Benzoxazolinone and Benzothiazoline‐2‐thione.

D'Amico

Bollinger

1990

ChemInform

View full text Add to dashboard Cite

Synthesis of 3‐substituted‐2‐benzothiazolinone, 2‐benzoxazolinone and benzothiazoline‐2‐thione

Cited by 9 publications

References 10 publications

Applying Ligands Profiling Using Multiple Extended Electron Distribution Based Field Templates and Feature Trees Similarity Searching in the Discovery of New Generation of Urea-Based Antineoplastic Kinase Inhibitors

Applying Ligands Profiling Using Multiple Extended Electron Distribution Based Field Templates and Feature Trees Similarity Searching in the Discovery of New Generation of Urea-Based Antineoplastic Kinase Inhibitors

Two Polymerizable Derivatives of 2,2‘-Azino-bis(3-ethylbenzthiazoline-6-sulfonic acid)

ChemInform Abstract: Synthesis of 3‐Substituted‐2‐benzothiazolinone, 2‐Benzoxazolinone and Benzothiazoline‐2‐thione.

Contact Info

Product

Resources

About