Synthesis and anticancer evaluation of novel 2-cyclopropylimidazo[2,1-b][1,3,4]-thiadiazole derivatives

Noolvi, Malleshappa N.; Patel, Harun; Singh, Navjot; Gadad, Andanappa K.; Cameotra, Swaranjit Singh; Badiger, Arvind

doi:10.1016/j.ejmech.2011.07.012

Cited by 108 publications

(36 citation statements)

References 15 publications

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“…Next, Knoevenagel condensation of aldehydes with malonic acid afforded pure (E)-acrylic acids. Finally, condensation of acrylic acids with various amines yielded ITDs (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13). Further, compound 13 was oxidized with m-CPBA and Oxone ® to yield sulfoxide 14 and sulfone 15.…”

Section: Synthesismentioning

confidence: 99%

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Structure–activity relationship of imidazothiadiazole analogs for the binding to the ecdysone receptor of insect cells

Yokoi¹,

Minami²,

Nakagawa³

et al. 2015

Pesticide Biochemistry and Physiology

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Diacylhydrazines are the first non-steroidal ecdysone agonists, and five compounds are used as insecticides in agriculture. After the discovery of diacylhydrazine-type compounds, numerous non-steroidal structures were reported as ecdysone agonists. Among various ecdysone agonists, imidazothiadiazoles are reported to be very potent in vitro; however, the experimental detail for the structure identification and bioassays are not stated in the paper (Holmwood and Schindler, Bioorg. Med. Chem. 17, 4064-4070, 2009). In our present study, we synthesized 18 imidazothiadiazole-type compounds and confirmed the chemical structures by spectrometric analyses. The binding activity of the synthesized compounds to the ecdysone receptor was evaluated in terms of the concentration required for 50% inhibition of [(3)H]ponasterone A incorporation [IC50 (M)] into lepidopteran (Sf-9), coleopteran (BCRL-Lepd-SL1), and dipteran (NIAS-AeAl2) cells. 6-(2-Chlorophenyl)-2-(trifluoromethyl)imidazo[2,1-b] [1,3,4]-thiadiazol-5-yl)acrylamide analogs with CONHR (secondary amide) were very potent against Sf-9 cells, but further alkylation (tertiary amide: CONR2) decreased the activity dramatically. Additionally, a primary amide analog (CONH2) was inactive. The activity also decreased 150-fold by the saturation of olefin region of the acrylamide moiety. In addition, various substituents were introduced at the 2-position of the imidazothiadiazole ring to disclose the physicochemical properties of the substituents which are important for receptor binding. The activity increased by 7500-fold with the introduction of the CF2CF2CF3 group compared to the unsubstituted compound against Sf-9 cells. Quantitative structure-activity relationship analysis for these substituents indicated that hydrophobic and electron-withdrawing groups were favorable for binding. Some of the compounds with strong receptor binding activity showed good larvicidal activity against Spodoptera litura. In contrast, the binding affinity of imidazothiadiazole analogs was low or not observed against dipteran and coleopteran cells.

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Section: Synthesismentioning

confidence: 99%

“…Mp: 174-175°C. 1 Other acrylamide analogs (3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13) were synthesized in a similar manner to that described for compound 2. Analytical data for the compounds are shown below.…”

Section: Thiadiazole (Step A)mentioning

confidence: 99%

Structure–activity relationship of imidazothiadiazole analogs for the binding to the ecdysone receptor of insect cells

Yokoi¹,

Minami²,

Nakagawa³

et al. 2015

Pesticide Biochemistry and Physiology

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“…(1972) and slightly modified. About 1 mL of nitroblue tetrazolium (NBT) solution (156 μM NBT in 100 mM phosphate buffer, pH 7.4), NADH solution (1 mL) (reduced form of β-nicotinamide adenine dinucleotide) (468 μM in 100 mM phosphate buffer, pH 7.4) and sample solution (0.1 mL) of compounds (10, 20, 30, 40, 50 and 100 μg) in distilled water were mixed and the reaction started by adding phenazine methosulphate (PMS) solution (100 μL) (60 μM PMS in 100 mM phosphate buffer, pH 7.4).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of 5-arylidine amino-1,3,4-thiadiazol-2-[(N-substituted benzyol)]sulphonamides endowed with potent antioxidants and anticancer activity induces growth inhibition in HEK293, BT474 and NCI-H226 cells

2013

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A series of imines 5-amino-1,3,4-thiadiazol-2-[(N-substituted benzyol)]sulphonamide derivatives were synthesized from various aromatic aldehydes and substituted with benzoyl acetazolamides under different reaction conditions and were evaluated for their antioxidant and free radical scavenging, antimitotic activity by Allium cepa meristem root model and cytotoxicity activity against HEK 293 (human epidermal kidney cell line), BT474 (breast cancer cell line) and NCI-H226 (lung cancer cell line) by MTT assay. Some of the synthesized compounds showed moderately potent cytotoxicity compared to indisulam. Graphical abstractA series of imines 5-amino-1,3,4-thiadiazol-2-[(N-substituted benzyol)]sulphonamide derivatives (9a–j); 5-amino-1,3,4-thiadiazol-2-[N-(substituted benzoyl)]sulphonamide (4a–g); 5-(4-acetamido phenyl sulphonamido)-1,3,4-thiadiazol-2-[N-(substituted benzoyl)]sulphonamide (6a–g); and 5-(4-amino phenyl sulphonamido)-1,3,4-thiadiazol-2-[N-(substituted benzoyl)]sulphonamide (7a–g) were synthesized from acetazolamide and were investigated for the in vitro anticancer by MTT assay, free radical scavenging and antimitotic activity by Allium cepa root meristem model. Experimental observations indicate that synthesized compounds were moderately potent anticancer agents.

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“…This motif is attached to main frame of the molecules at different ways. Cyclopropyl group is connected to C‐atom in heterocyclic fragment or nitrogen atom in ciprofloxacin derivatives, to carbon chain of C 29 sterols, as 1,1‐dichloro derivatives of diaryl cyclopropanes . It is also present in combretastatin derivatives as cyclopropyl‐vinyl or a cyclopropyl‐amide bridge, in cyclopropyl indolequinones or cinnamic acid derivatives …”

Section: Introductionmentioning

confidence: 99%

Cytotoxic and Antimicrobial Activity of Dehydrozingerone based Cyclopropyl Derivatives

Burmudžija

Muškinja

Kosanić

et al. 2017

Chemistry & Biodiversity

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A small series of 1-acetyl-2-(4-alkoxy-3-methoxyphenyl)cyclopropanes was prepared, starting from dehydrozingerone (4-(4-hydroxy-3-methoxyphenyl)-3-buten-2-one) and its O-alkyl derivatives. Their microbiological activities toward some strains of bacteria and fungi were tested, as well as their in vitro cytotoxic activity against some cancer cell lines (HeLa, LS174 and A549). All synthesized compounds showed significant antimicrobial activity and expressed cytotoxic activity against tested carcinoma cell lines, but they showed no significant influence on normal cell line (MRC5). Butyl derivative is the most active on HeLa cells (IC = 8.63 μm), while benzyl one is active against LS174 and A549 cell lines (IC = 10.17 and 12.15 μm, respectively).

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Synthesis and anticancer evaluation of novel 2-cyclopropylimidazo[2,1-b][1,3,4]-thiadiazole derivatives

Cited by 108 publications

References 15 publications

Structure–activity relationship of imidazothiadiazole analogs for the binding to the ecdysone receptor of insect cells

Structure–activity relationship of imidazothiadiazole analogs for the binding to the ecdysone receptor of insect cells

Synthesis of 5-arylidine amino-1,3,4-thiadiazol-2-[(N-substituted benzyol)]sulphonamides endowed with potent antioxidants and anticancer activity induces growth inhibition in HEK293, BT474 and NCI-H226 cells

Cytotoxic and Antimicrobial Activity of Dehydrozingerone based Cyclopropyl Derivatives

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