22915-25-9Relevant academic research and scientific papers
Microwave-assisted synthesis of some novel thiazolidinone and thiohydantoin derivatives of isatins
Raghuvanshi, Dushyant Singh,Singh, Krishna Nand
, p. 2243 - 2248 (2010)
A simple, rapid, and efficient method for the synthesis of some new thiazolidinone and thiohydantoin derivatives of isatins along with some Mannich bases has been achieved in excellent yield from indole-2,3-dione-3- thiosemicarbazone employing microwave irradiation. Copyright Taylor & Francis Group, LLC.
Synthesis of some new spiro, isolated and fused heterocycles based on 1H-indole-2-one
El-Emary,Ahmed,Bakhite
, p. 921 - 927 (2001)
The reaction of 3-benzoylcyanomethylidine-1(H)-indole-2-one (1) with a variety of active methylene compounds, thioglycolic acid, glycine, hydrazine hydrate and phenyl hydrazine led to the formation of compounds 4a-d-10. 3-Thiosemicarbazide-1(H)-indole-2-one 2 on reaction with α-halocarbonyl compounds gave compounds 11a-c, 12a-c. The latter compounds on heating with phosphoryl chloride, cyclization takes place via losing water to give the angular tetracyclic compounds 13a,b and 14a-c. Cyanoacetic hydrazone derivative 3 readily cyclized upon heating in triethyl orthoformate to give the tricyclic system, oxopyridazino indole 15. On the other hand, the reaction of 3 with benzylidine malononitrile and benzylidene ethylcyanoactate gave the pyranyl hydrazone derivatives 16a,b.
Insight on a new indolinone derivative as an orally bioavailable lead compound against renal cell carcinoma
Fouad, Marwa A.,Zaki, Mayssoune Y.,Lotfy, Raghda A.,Mahmoud, Walaa R.
, (2021/06/15)
A series of novel 3-indolinone-thiazolidinones and oxazolidinones 4a-k was synthesized via molecular hybridization approach and sequentially evaluated to explore its cytotoxic activity. The cytotoxicity screening pointed toward the N-cyclohexyl thiazolidinone derivative 4f that revealed promising renal cytotoxicity against CAKI-1 and UO-31 renal cancer cell lines with IC50 values 4.74 and 3.99 μM, respectively, which were comparable to those of sunitinib along with good safety threshold against normal renal cells. Further emphasis on compound 4f renal cytotoxicity was achieved via different enzyme assays and CAKI-1 and UO-31 cell cycle analysis. The results were supported by in silico studies to explore its physicochemical, pharmacokinetic and drug-likeness properties. Finally, compound 4f was subjected to an in vivo pharmacokinetic study through two different routes of administration showing excellent oral bioavailability. This research represents compound 4f as a promising candidate against renal cell carcinoma.
Synthesis of some new heterocyclic compounds derived from 3-formylchromones and their antimicrobial evaluation
Bari,Ali,Kadi,Hashmi,Ng
, p. 1723 - 1731 (2014/05/06)
The synthesis and antimicrobial evaluation of a series of chromone-linked substituted heterocyclic derivatives is described. The condensation of 3-formylchromone with acetoacetamide under Knoevenagel-Cope reaction conditions was also explored, and the condensation with 4-hydroxy-6-methyl-2H-pyran-2-one constitutes a facile route to pyranopyrone fused systems. Most of the compounds exhibit good antimicrobial properties.
A convenient synthesis of some new indole containing thiazolidinone, thiohydantoin, triazine and its derivatives with ethoxyphthalimide moiet
Hussain, Nasir,Joshi, Ajit,Sharma, Chirag,Talesara, G. L.
, p. 5917 - 5921,5 (2020/09/15)
Acid catalyzed condensation of thiosemicarbazide with indole-2,3-dione (isatin) yielded indole-2,3-dione-3-thiosemicarbazone (1). 3- [(1,3-Thiazolidin-4-one-2-yl)hydrazido]-indole-2-one (2) and 3-[(2-thioxoimidazolidin-4-one-3-yl)imino]-indole-2-one (3) were obtained by condensation of (1) with chloroacetic acid under different conditions. Compounds (2) and (3) on interaction with various aromatic aldehydes afforded the corresponding 5-substituted benzylidene derivatives (4a-d) and (5a-d) respectively, which on refluxing with bromoethoxyphthalimide furnished the corresponding 3-[(5-(4-substitutedbenzylidene)-3-N-ethoxyphthalimido-1,3- thiazolidin-4-one- 2-yl) hydrazido]-1-N-ethoxyphthalimido-indole-2-one (6a-d) and 3-[(5-(4-substitutedbenzylidene)-2-phthalimidoxyethylsulfanylimidazolin- 4-one-3-yl)imino]-1-N-ethoxyphthalimido-indole-2-one (7a-d). Compound (1) was also cyclized with KOH in absolute ethanol to yield 2,5-dihydro-3H-[1,2,4] triazino[5,6-b]indole-3-thione (8). Subsequent treatment with bromoethoxyphthalimide yielded 3- (phthalimidoxyethylsulfanyl)-5-N- ethoxyphthalimido-[1,2,4]triazino[5,6-b]indole (9). All the synthesized compounds were characterized by their spectral and elemental analysis data.
Oxindole derivatives as inhibitors of TAK1 kinase
Lockman, Jeffrey W.,Reeder, Matthew D.,Robinson, Rosann,Ormonde, Patricia A.,Cimbora, Daniel M.,Williams, Brandi L.,Willardsen, J. Adam
scheme or table, p. 1724 - 1727 (2011/05/04)
Several series of oxindole analogues were synthesized and screened for inhibitory activity against transforming growth factor-β-activating kinase 1 (TAK1). Modifications around several regions of the lead molecules were made, with a distal hydroxyl group
Synthesis and in vitro evaluation of some isatin-thiazolidinone hybrid analogues as anti-proliferative agents
Ramshid,Jagadeeshan, Sankar,Krishnan, Anand,Mathew, Mary,Nair, S. Asha,Pillai, M. Radhakrishna
experimental part, p. 306 - 312 (2011/09/13)
A range of isatin-thiazolidinone hybrid analogues were synthesized and their cytotoxicity was evaluated against several cancer cell lines in vitro. The acute toxicity studies in mice models revealed that these analogues possess low systemic toxicity and are safe up to 1600mg/Kg. Among the compounds synthesized, 5-(2-nitrobenzylidene)-2-(isatin-3- azino)-thiazolidin-4-one (CI) has been shown to be the most active, highly promising compound which induced S phase arrest in cell cycle in a time dependent manner. Our initial analysis indicate that incorporation of electron withdrawing group at ortho position of the ring favors over the meta and para positions for eliciting its cytostatic effect. Overall, the in vitro biological evaluation suggests that the growth inhibitory effect of CI is promising and can be studied further.
Synthesis of Some New Thiazolidinone and 2-Thiohydantoin Derivatives Bearing an Isatin Moiety
Mahmoud, A.M.,Abdel-Rahman, A.E.,El-Naggar, G.M.,El-Sherief, H.A.
, p. 379 - 381 (2007/10/02)
2-(Isatin-3-azino)-4-thiazolidinone (I) and 1-(isatin-3-imino)-2-thiohydantoin (III) have been obtained by condensation of isatin-3-thiosemicarbazone with chloroacetic acid under different conditions.Compounds I and III on interaction with aromatic or heterocyclic aldehydes afford 5-arylidene-2-(isatin-3-azino)thiazolidinones (II) and 5-arylidene-3-(isatin-3-imino)-2-thiohydantoins (IV) respectively.These compounds (II, IV) have been screened for their antimicrobial activities.
