Synthesis and evaluation of pyrazolines bearing benzothiazole as anti-inflammatory agents

Kharbanda, Chetna; Alam, Mohammad Sarwar; Hamid, Hinna; Javed, Kalim; Bano, Sameena; Dhulap, Abhijeet; Ali, Yakub; Nazreen, Syed; Haider, Saqlain

doi:10.1016/j.bmc.2014.09.028

Cited by 79 publications

(34 citation statements)

References 35 publications

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“…[25] It has been assumed by Regulski et al [26] that inflammation produces the appropriate conditions for genetic changes. Drugs containing pyrazole ring, the core scaffold in a number of selective COX-2 inhibitors [30][31][32][33][34][35][36][37][38][39][40][41] such as celecoxib and SC-558 (Scheme 1), [42,43] have been established as successful candidates for selective COX-2 inhibition. Oxidative stress may lead to DNA mutations resulting into uncontrolled proliferation and resistance to apoptosis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new pyrazolo[3,4‐d]pyrimidine derivatives and evaluation of their anti‐inflammatory and anticancer activities

et al. 2017

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This study reports the synthesis of two series of new purine bioisosteres comprising a pyrazolo[3,4-d]pyrimidine scaffold linked to piperazine moiety through different amide linkages. The newly synthesized compounds were evaluated for anticancer activity against four cell lines (MDA-MB-231, MCF-7, SF-268, B16F-10) and cyclooxygenase (COX-2) protein expression inhibition in lipopolysaccharide (LPS)-activated rat monocytes. The results revealed that most of the synthesized compounds showed moderate-to-high cytotoxic activity against at least one cell line, with compound 10b being the most active against all used cell lines (IC values 5.5-11 μg/ml) comparable to cisplatin. In addition, six of these compounds (7b, 10a-d, and 12c) demonstrated inhibition of LPS-induced COX-2 protein expression at low concentration (25 μg/ml) as compared to the control non-stimulated cells and showed a COX-2 selectivity index range comparable to diclofenac sodium. The overall results indicate that many of these pyrazolopyrimidine derivatives possess in vitro anti-inflammatory and anticancer activities at varying doses, and the most active compounds will be subjected to in vivo pharmacological evaluation.

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Section: Introductionmentioning

confidence: 99%

Synthesis of new pyrazolo[3,4‐d]pyrimidine derivatives and evaluation of their anti‐inflammatory and anticancer activities

et al. 2017

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“…They are associated with various biological activities, for example, anticancer activity , because of inhibition of vital enzymes, namely, cytochrome P450 enzyme , EGFR tyrosine kinase , or COX‐2 enzyme . In addition, these derivatives are considered as antimicrobial , anti‐inflammatory , antioxidant , antitubercular , and antimalarial agents. Moreover, incorporation of thiophene nucleus at position 2 of benzothiazole gives rise to compounds possessing potent anticancer and antimicrobial activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Evaluation of Some Novel Thiophene, Thieno[3,2‐d]pyrimidine, Thieno[3,2‐b]pyridine, and Thieno[3,2‐e][1,4]oxazepine Derivatives Containing Benzothiazole Moiety

Hassan

Husseiny

2019

Journal of Heterocyclic Chem

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In an attempt to establish novel candidate with promising anticancer activity, two derivatives of (benzo[d]thiazol‐2‐yl)thiophene backbone 1 and 14 were synthesized, and they further reacted with various chemical reagents to afford the corresponding substituted thiophene derivatives 6, 8, 10, 15, 17, and 20, thieno[3,2‐d]pyrimidine derivatives 2–5, 7, 9, 16, 21, 23, and 24, thieno[3,2‐b]pyridine derivatives 11–13, and thieno[3,2‐e][1,4]oxazepine derivative 18. Structures of prepared compounds were affirmed via spectral and elemental data. Among the obtained compounds, seven derivatives 2, 3, 4, 5, 11, 12, and 13 were chosen by National Cancer Institute, USA. Such compounds were screened for their antitumor activity versus 60 cancer cell lines in one‐dose (10 μmol) screening assay. The outcomes showed that all selected compounds exhibited moderate to high anticancer activity towards many cancer cell lines among which compounds 5 and 11 exerted potent antitumor activity against numerous malignant growth cell lines particularly Ovarian Cancer IGROV1.

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“…They have absorbed a great deal of attention in pharmacological industry due to their wide spectrum of biological activities . Benzothiazole derivatives have also been found to possess good anti‐inflammatory activity including good p38α MAP kinase inhibition …”

Section: Introductionmentioning

confidence: 99%

Synthesis, p38α MAP kinase inhibition, anti‐inflammatory activity, and molecular docking studies of 1,2,4‐triazole‐based benzothiazole‐2‐amines

Tariq¹,

Alam²,

Amir³

2018

Archiv der Pharmazie

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Recent studies have demonstrated that inhibition of p38α MAP kinase could effectively inhibit pro-inflammatory cytokines including TNF-α and interleukins. Thus, inhibition of this enzyme can prove greatly beneficial in the therapy of chronic inflammatory diseases. A new series of N-[3-(substituted-4H-1,2,4-triazol-4-yl)]-benzo[d]thiazol-2-amines (4a-n) were synthesized and subjected to in vitro evaluation for anti-inflammatory activity (BSA anti-denaturation assay) and p38α MAPK inhibition. Among the compounds selected for in vivo screening of anti-inflammatory activity (4b, 4c, 4f, 4g, 4j, 4m, and 4n), compound 4f was found to be the most active with an in vivo anti-inflammatory efficacy of 85.31% when compared to diclofenac sodium (83.68%). It was also found to have a low ulcerogenic risk and a protective effect on lipid peroxidation. The p38α MAP kinase inhibition of this compound (IC = 0.036 ± 0.12 μM) was also found to be superior to the standard SB203580 (IC = 0.043 ± 0.27 μM). Furthermore, the in silico binding mode of the compound on docking against p38α MAP kinase exemplified stronger interactions than those of SB203580.

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Synthesis and evaluation of pyrazolines bearing benzothiazole as anti-inflammatory agents

Cited by 79 publications

References 35 publications

Synthesis of new pyrazolo[3,4‐d]pyrimidine derivatives and evaluation of their anti‐inflammatory and anticancer activities

Synthesis of new pyrazolo[3,4‐d]pyrimidine derivatives and evaluation of their anti‐inflammatory and anticancer activities

Synthesis and Anticancer Evaluation of Some Novel Thiophene, Thieno[3,2‐d]pyrimidine, Thieno[3,2‐b]pyridine, and Thieno[3,2‐e][1,4]oxazepine Derivatives Containing Benzothiazole Moiety

Synthesis, p38α MAP kinase inhibition, anti‐inflammatory activity, and molecular docking studies of 1,2,4‐triazole‐based benzothiazole‐2‐amines

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