Synthesis and antitumor evaluation of novel Benzo[d]pyrrolo[2,1-b]thiazole derivatives

Chaniyara, Ravi; Tala, S. D.; Chen, Chi‐Wei; Lee, Pei‐Chih; Kakadiya, Rajesh; Dong, Honglin; Marvania, Bhavin; Chen, Ching Huang; Chou, Ting‐Chao; Lee, Te‐Chang; Shah, Anamik; Su, Tingwei

doi:10.1016/j.ejmech.2012.03.030

Cited by 38 publications

(30 citation statements)

References 17 publications

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“…CL141, CL1-5, CL100, CL97, PC9, PC9/gef B4 [24] , and CL1-5/GFP-Luciferase [25] lines were kindly provided by Dr. Pan-Chyr Yang (National Taiwan University, Taipei, Taiwan). CL141T was derived from CL141 xenograft from a NOD-SCID mouse in our laboratory [26] . The luciferase overexpressed H1650 cells, designated as H1650-Luc cells, were established by transfection of 2.5 μg of pGL4.10[ Luc 2] plasmid DNA (Promega) into H460 cells using 5 μl of Lipofectamine 2000 Reagent (Invitrogen) for 4 hours and cultured with 1 mg/ml of geneticin (Gibco).…”

Section: Methodsmentioning

confidence: 99%

“…Formation of DNA cross-links was analyzed by alkaline agarose gel electrophoresis as previously described [26] . Briefly, purified pEGFP-N1 plasmid DNA (1500 ng) was mixed with various concentrations (0.125 to 2 μM) of BO-1978 or cisplatin in 40 μl of binding buffer (3 mM sodium chloride, 1 mM sodium phosphate, pH 7.4, and 1 mM EDTA).…”

Section: Methodsmentioning

confidence: 99%

“…The response of DNA damage biomarker (γH2AX) and proteins involved in repair of DNA double-strand breaks (DNA-dependent protein kinase [DNA-PK] and Rad51) and apoptosis (caspase 3 and 7 and poly-ADP ribose polymerase [PARP]) to BO-1978 was determined by Western blotting [26] . Briefly, H460 cells were treated with various concentrations of BO-1978 for 72 hours or 2 μM for different time periods.…”

Section: Methodsmentioning

confidence: 99%

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A Potent Derivative of Indolizino[6,7-b]Indole for Treatment of Human Non–Small Cell Lung Cancer Cells

Chen

et al. 2016

Neoplasia

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The therapeutic effect in non–small cell lung cancer (NSCLC) patients is limited because of intrinsic and acquired resistance. Thus, an unmet need exists for the development of new drugs to improve the therapeutic efficacy in NSCLC patients. In this study, the novel small molecule indolizino[6,7-b]indole derivative BO-1978 was selected to evaluate its therapeutic effects on NSCLC and its preclinical toxicity in animal models. An in vitro cytotoxicity assay revealed that BO-1978 significantly suppressed the growth of various NSCLC cell lines with or without mutations in epidermal growth factor receptor (EGFR). Mechanistically, we demonstrated that BO-1978 exhibited multiple modes of action, including inhibition of topoisomerase I/II and induction of DNA cross-linking. Treatment of NSCLC cells with BO-1978 caused DNA damage, disturbed cell cycle progression, and triggered apoptotic cell death. Furthermore, BO-1978 significantly suppressed the growth of EGFR wild-type and mutant NSCLC tumors in xenograft tumor and orthotopic lung tumor models with negligible body weight loss. The combination of BO-1978 with gefitinib further suppressed EGFR mutant NSCLC cell growth in xenograft tumor and orthotopic lung tumor models. Preclinical toxicity studies showed that BO-1978 administration did not cause apparent toxicity in mice. Based on its significant therapeutic efficacy and low drug toxicity, BO-1978 is a potential therapeutic agent for treatment of NSCLC.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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A Potent Derivative of Indolizino[6,7-b]Indole for Treatment of Human Non–Small Cell Lung Cancer Cells

Chen

et al. 2016

Neoplasia

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“…1,3-Thiazoles undergo different types of reactions to yield various biologically active fused heterocyclic moieties as thiazolopyrimidine, imidazothiazoles, thiazolopyridine, etc. [19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Thiazole Derivatives

Ibrahim¹,

Rizk²

2021

Azoles - Synthesis, Properties, Applications and Perspectives

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Thiazoles belong to the group of azole heterocycles. They are aromatic five-membered heterocycles containing one sulfur and one nitrogen atom. In recent years thiazoles, their derivatives, and isomers have gained considerable attention because of their broad applications in different fields, such as agrochemicals, industrial, and photographic sensitizers. Also, they have pharmaceutical and biological activities that include antimicrobial (sulfazole), antiretroviral (ritonavir), antifungal (abafungin), anticancer (tiazofurin), antidiabetic, anti-inflammatory, anti-Alzheimer, antihypertensive, antioxidant, and hepatoprotective activities. The compounds containing thiazole moieties are a prominent structural feature in a variety of natural products, such as vitamin B and penicillin. Thus, in this chapter several types of thiazole-based heterocyclic scaffolds such as monocyclic or bicyclic systems synthesis and their biological activities studies are presented. Furthermore modification of thiazole-based compounds at different positions to generate new molecules with potent antitumor, antioxidant, and antimicrobial activities is described.

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“…It has been reported that pyrrolo[2,1- b ]thiazole derivatives have been used as hepatoprotective, antidiabetic, antibiotic, anticonvulsant, antiinflammatory, bactericides and antitumor agents123456. Therefore, many efficient synthetic methods have been exploited for the synthesis of diverse pyrrolo[2,1- b ]thiazole and its bezno- derivatives7891011121314151617.…”

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confidence: 99%

Stepwise cycloaddition reaction of N-phenacylbenzothiazolium bromides and nitroalkenes for tetrahydro-, dihydro- and benzo[d]pyrrolo[2,1-b]thiazoles

Jin

Sun

Yang

et al. 2017

Sci Rep

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The triethylamine promoted stepwise 1,3-dipolar cycloaddition reaction of N-phenacylbenzothiazolium bromides with nitroalkenes in ethanol resulted in a mixture of two isomeric tetrahydrobenzo[d]pyrrolo[2,1-b]thiazoles with cis/trans/cis- and all-trans-configurations. More importantly, the corresponding dihydrobenzo[d]pyrrolo[2,1-b]thiazoles can be selectively prepared in refluxing ethanol and the benzo[d]pyrrolo[2,1-b]thiazoles can be obtained in satisfactory yields by sequential dehydrogenation with DDQ as oxidizer. On the other hand, the similar cycloaddition reaction of N-phenacylbenzothiazolium bromides with 1-methy-1-nitroalkenes in refluxing ethanol afforded benzo[d]pyrrolo[2,1-b]thiazoles with splitting out of nitro group. The stereochemistry of the spiro compounds was clearly elucidated on the basis of NMR spectra and sixteen single crystal structures.

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Synthesis and antitumor evaluation of novel Benzo[d]pyrrolo[2,1-b]thiazole derivatives

Cited by 38 publications

References 17 publications

A Potent Derivative of Indolizino[6,7-b]Indole for Treatment of Human Non–Small Cell Lung Cancer Cells

A Potent Derivative of Indolizino[6,7-b]Indole for Treatment of Human Non–Small Cell Lung Cancer Cells

Synthesis and Biological Evaluation of Thiazole Derivatives

Stepwise cycloaddition reaction of N-phenacylbenzothiazolium bromides and nitroalkenes for tetrahydro-, dihydro- and benzo[d]pyrrolo[2,1-b]thiazoles

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