Synthesis of 2-anilinopyridyl linked benzothiazole hydrazones as apoptosis inducing cytotoxic agents

Sultana, Faria; Saifi, Mohd Aslam; Syed, Rabbani; Mani, Ganesh Kumar; Shaik, Siddiq Pasha; Egharevba, Godshelp Osas; Godugu, Chandraiah; Shahjahan, Syeda; Kamal, Ähmed

doi:10.1039/c8nj06517a

Cited by 23 publications

(13 citation statements)

References 24 publications

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“…2-Aminobenzothiazoles demonstrate high antiviral activity [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 ], which is especially important in this period of global COVID-19 pandemic. They also possess antimicrobial [ 14 , 15 , 16 , 17 , 18 , 19 , 20 ], antioxidant [ 20 ], anti-inflammatory [ 21 , 22 , 23 , 24 ], analgesic [ 24 ], antidepressant [ 25 , 26 ], anticonvulsant [ 27 , 28 , 29 ], anti-diabetic [ 21 , 30 ], antitumor [ 31 , 32 , 33 , 34 , 35 ], antituberculosis [ 14 , 36 ] activity. Their derivatives show also antimalarial [ 37 , 38 ], insecticide [ 39 ] and herbicide effect [ 40 ].…”

Section: Aminobenzothiazolesmentioning

confidence: 99%

“…Replacement of the amino group in 2-aminobenzothiazoles by the hydrazine residue opens the way to numerous hydrazones whose chemistry is thoroughly studied. An example of such an approach was demonstrated by the synthesis of 6-substituted 2-hydrazinobenzothiazoles by the reaction of the corresponding 2-aminobenzothiazoles with hydrazine hydrate followed by the reaction with various 2-(arylamino)nicotinealdehydes ( Scheme 37 ) [ 34 ]. The products 45a – v possess antiproliferative activity.…”

Section: Aminobenzothiazolesmentioning

confidence: 99%

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Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives

2021

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The review is devoted to modern trends in the chemistry of 2-amino and 2-mercapto substituted benzothiazoles covering the literature since 2015. The reviewed heterocycles belong to biologically active and industrially demanded compounds. Newly developed synthesis methods can be divided into conventional multistep processes and one-pot, atom economy procedures, realized using green chemistry principles and simple reagents. The easy functionalization of the 2-NH2 and 2-SH groups and the benzene ring of the benzothiazole moiety allows considering them as highly reactive building blocks for organic and organoelement synthesis, including the synthesis of pharmacologically active heterocycles. The review provides a summary of findings, which may be useful for developing new drugs and materials and new synthetic approaches and patterns of reactivity.

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Section: Aminobenzothiazolesmentioning

confidence: 99%

Section: Aminobenzothiazolesmentioning

confidence: 99%

Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives

2021

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“…Cancer follows a variety of mutagenic processes which permit cancer cells to gain extraordinary proliferation potential, self‐sufficiency in growth signals and resistance to both anti‐proliferative and apoptotic cues which would otherwise contain their growth 4,5 . Proteins that regulate apoptosis can be potential cancer drug targets 6 . Apoptosis inducers and cytotoxic agents represent a wide spectrum of classical molecules having anticancer ability 6 .…”

Section: Introductionmentioning

confidence: 99%

“…4,5 Proteins that regulate apoptosis can be potential cancer drug targets. 6 Apoptosis inducers and cytotoxic agents represent a wide spectrum of classical molecules having anticancer ability. 6 Treating cells with cytotoxic agents can cause decrease in cell viability or the cells can activate apoptosis.…”

Section: Introductionmentioning

confidence: 99%

“…6 Apoptosis inducers and cytotoxic agents represent a wide spectrum of classical molecules having anticancer ability. 6 Treating cells with cytotoxic agents can cause decrease in cell viability or the cells can activate apoptosis. Henceforth, investigation on cytotoxic potential paves way for an efficient method for the development of anticancer agents.…”

Section: Introductionmentioning

confidence: 99%

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Novel synthetic aromatic thiourea derivatives and investigations on their cytotoxic potential efficacy

Ray

John

Pooppadi

et al. 2020

Journal of Heterocyclic Chem

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Aromatic thiourea derivatives were synthesized by standard reactions from isothiocyanates in high yield. An efficient one‐pot synthesis of primary amine with carbon disulfide involving the intermediate dithiocarbamate conversion using T3P (propane phosphonic anhydride) to isothiocyanate is reported. Newly synthesized compounds showed excellent luminescence property. Cytotoxic investigation with different human cancer cell lines showed IC50 values varying from of 17 to 40 μM for N‐phenethyl‐3,4‐dihydroisoquinoline‐2(1H)‐carbothioamide (SCR172) among other molecules. Increase in Sub G1 population and increased depolarisation of mitochondria were evident in cells treated with SCR172, suggesting its role as a cancer therapeutic agent. This provides a lead structure for further synthetic modifications.

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Design, synthesis, biological evaluation, and in silico studies of 2‐aminobenzothiazole derivatives as potent PI3Kα inhibitors

Haider

Ahmad

Najmi

et al. 2022

Archiv der Pharmazie

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A new series of 2-aminobenzothiazole derivatives was designed, synthesized and evaluated for their anticancer activity against the MCF7, MDAMB-231, and HepG2 cancer cell lines. All synthesized derivatives (8a-8n) demonstrated moderate to high anticancer activity against the tested cell lines. As the most potent compound in the series, compound 8i displayed excellent inhibitory potency with an IC 50 value of 6.34 μM and compound 8m displayed an IC 50 value of 8.30 µM against the MCF7 cell line compared to the standard drug HS-173 (IC 50 = 10.25 μM). PI3K enzyme activity assays demonstrated that compound 8i is highly selective against PI3Kα, with an IC 50 value of 1.03 nM. Wound healing assays and cell cycle analysis of compounds 8i and 8m revealed that both compounds suppressed the migration of MCF7 cells and induce cell cycle arrest in the S phase. In the cell death assay, compound 8i was revealed to induce apoptosis in a dose-dependent pattern; further Western blot assays revealed that compound 8i obviously decreases the levels of the antiapoptotic proteins Bcl-xL and Mcl-1. Downregulation of the expression of p-Akt confirmed the PI3K inhibitory activity of compound 8i. The molecular docking and molecular dynamics simulation studies performed were found in agreement with the PI3Kα inhibitory activity assessments performed experimentally.

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Synthesis of 2-anilinopyridyl linked benzothiazole hydrazones as apoptosis inducing cytotoxic agents

Abstract: A series of 2-anilinopyridyl linked benzothiazole-hydrazone conjugates (5a-aa) were designed, synthesized and evaluated for their anticancer potential.

Cited by 23 publications

References 24 publications

Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives

Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives

Novel synthetic aromatic thiourea derivatives and investigations on their cytotoxic potential efficacy

Design, synthesis, biological evaluation, and in silico studies of 2‐aminobenzothiazole derivatives as potent PI3Kα inhibitors

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