153595-93-8Relevant articles and documents
Indole-coumarin-thiadiazole hybrids: An appraisal of their MCF-7?cell growth inhibition, apoptotic, antimetastatic and computational Bcl-2 binding potential
Kamath, Pooja R.,Sunil, Dhanya,Joseph, Manu M.,Abdul Salam, Abdul Ajees,T.T., Sreelekha
, p. 442 - 451 (2017)
Cancer therapeutic potential of thiadiazole hybrids incorporating pharmacologically active indole and coumarin moieties have not been explored much. In the current investigation, three new thiadiazole hybrids with spacers of varying lengths linking indole and thiadiazole units were synthesized and their structures were well-established using various spectroscopic techniques. 3-(1-(5-(3-(1H-indol-3-yl)propyl)-1,3,4-thiadiazol-2-ylimino)ethyl)-6-bromo-2H-chromen-2-one (IPTBC) exhibited dose-dependent cytotoxicity in breast adenocarcinoma (MCF-7) cells. The circumvention of apoptosis is a prominent hallmark of cancer and hence triggering apoptosis in specific cancer cells is one of the convenient and widely used approaches for the development of anticancer chemotherapeutics. The induction of apoptosis upon treatment with IPTBC was confirmed by multiple apoptosis assays like Acridine orange-ethidium bromide, Hoechst staining, TUNEL staining, and colorimetric quantification using APOPercentage Apoptosis assay. The apoptosis initialisation through the active involvement of caspases was confirmed by caspase profiling tests. The wound healing assay displayed an intense impairment in the motility of MCF-7?cells suggesting the anti-metastatic potential of IPTBC. The ability of IPTBC to inhibit the antiapoptotic Bcl-2 protein by acting as a small molecule BH3 mimetic was explored through docking simulation studies. Although auxiliary investigations are warranted with this promising thiadiazole hybrid IPTBC, the perspective anticancer potential through programmed cell death, anti-metastatic and probable Bcl-2 inhibitory action will enable its further exploration in oncology.
Novel indole-based melatonin analogues substituted with triazole, thiadiazole and carbothioamides: studies on their antioxidant, chemopreventive and cytotoxic activities
Shirinzadeh, Hanif,Ince, Elif,Westwell, Andrew D.,Gurer-Orhan, Hande,Suzen, Sibel
, p. 1312 - 1321 (2016/10/09)
Melatonin (MLT) is a well-known free-radical scavenger, involving in the prevention of cellular damage that can lead to cancer, ageing and a variety of neurodegenerative diseases. Research on MLT-related compounds has been required to optimise the maximum
Synthesis and anticonvulsant evaluation of some novel 2,5-disubstituted 1,3,4-thiadiazoles: pharmacophore model studies
Rajak, Harish,Behera, Chinmay Kumar,Pawar, Rajesh Singh,Singour, Pradeep Kumar,Kharya, Murli Dhar
, p. 503 - 510 (2011/05/14)
A novel series of N1-{5-[(1H-indol-3-ylmethyl)-1,3,4-thiadiazol- 2-yl}-N4-(4-substituted benzaldehyde)-semicarbazones, N 1-{5-[(1H-indol-3-ylmethyl)-1,3,4-thiadiazol-2-yl}-N 4-[1-(4-substituted phenyl)ethanone]-
THIADIAZOLE DERIVATIVES, INHIBITORS OF STEAROYL-COA DESATURASE
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Page/Page column 60, (2008/12/07)
The present invention relates to substituted thiadiazole compounds of the formula (I) and pharmaceutically acceptable salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds for modulating SCD activity.
Synthesis of newer indolyl/phenothiazinyl substituted 2-oxo/thiobarbituric acid derivatives as potent anticonvulsant agents
Archana,Rani, Preeti,Bajaj, Kiran,Srivastava, Virendra Kishore,Chandra, Ramesh,Kumar, Ashok
, p. 301 - 306 (2007/10/03)
2-Amino-5-(heteroarylmethylene)-1,3,4-oxadiazoles/thiadiazoles 7-10 were synthesized by cyclisation of 1-(heteroarylacetyl)semicarbazides/thiosemicarbazides 3-6. 5-(2′-Heteroarylmethylene-5′-aminomethylene-1′, 3′, 4′-oxadiazol-2′-yl/thiadiazol-2′-yl)-2-oxo/thiobarbituric acids 11-18 were synthesized by condensation of compounds 7-10 at the 5th position of 2-oxo/thiobarbituric acids. The newly synthesized compounds showed anticonvulsant activity ranging from 50-90% (seizures protection). Compound 18 (5-(2′-phenothiazinylmethylene-5′- aminomethylene-1′3′,4′-thiadiazol-2′-yl)-2- thiobarbituric acid) showed maximum activity being more potent than the reference drug phenytoin sodium (CAS 630-93-3).
Synthesis of some newer indolyl-thiadiazolyl-pyrazolines and indolyl-oxadiazolyl-pyrazolines as potential anti-inflammatory agents
Sharma, Shalabh,Srivastava, Virendra Kishor,Kumar, Ashok
, p. 2647 - 2654 (2007/10/03)
Some new 1-acetyl-5-substitutedaryl-3-[5′-(3″ -indolylmethyl)-2′-amino-1′,3′,4′,-thiadiazol- 2′N-yl]-2-pyrazolines 6a-6e and 1-acetyl-5-substitutedaryl-3-[5′-(3″-indolylmethyl)-2′- amino-1′,3′,4′-oxadiazol-2′N-yl]-2-pyrazolines 6′a-6′e have been synthesized by 5-(3′-indolymethyl)-1,3,4-thiadiazolyl)-2-aminosubstitutedchalkones 5a-5e and 5-(3′-indolylmethyl)-1,3,4-oxadiazolyl-2-aminosubstitutedchalkones 5′a-5′e, respectively. All these compounds of the present series have been screened for their anti-inflammatory activity. Compounds 6c and 6′c are found to be most active compound of this series, which show 47.6% and 49.0% inflammation inhibitory activity at a dose of 50 mg/kg p.o., while standard drug phenylbutazone exhibit 45.6% anti-inflammatory activity at same dose. The structure of these compounds has been illustrated by IR and 1H NMR spectra.
Synthesis of diheteroarylmethanes from activated nitriles
Ram, Vishnu Ji,Nath, Mahendra
, p. 394 - 398 (2007/10/03)
Novel procedures for the synthesis of diheteroarylmethanes 3-7 have been developed from the base-catalysed condensation-cyclization reactions of (indol-3-yl)methylmalononitrile 2 with amidine, dicyandiamide, hydroxylamine, hydrazine and thioglycolic acid separately. The acid catalysed reaction of 1 and 9 with thiosemicarbazide separately affords 8 and 10. The latter on reaction with phenacyl bromide yield 11. Base-catalysed reaction of 9 with dicyandiamide gives symmetrical triazine 14.
SYNTHESIS OF DERIVATIVES OF 1,3,4-OXA(THIA)DIAZOLE AND 1,2,4-TRIAZOLE CONTAINING 3-INDOLYLMETHYL RADICALS
Kelarev, V. I.,Karakhanov, R. A.,Gasanov, S. Sh.,Morozova, G. V.,Kuatbekova, K. P.
, p. 323 - 329 (2007/10/02)
Depending on the reaction conditions, 1,2,4-triazoline-3-thiones, 2-amino-1,3,4-thiadiazoles, or 2-amino-1,3,4-oxadiazoles with 3-indolylmethyl radicals are formed during the heterocyclization of 1-(3-indolylacetyl)thiosemicarbazides.Substituted 1,2,4-tri
