- Stereoselective synthesis of spirocyclic pyrrolidines/pyrrolizidines/pyrrolothiazolidines using l-proline functionalized manganese ferrite nanorods as a novel heterogeneous catalyst
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An efficient, green, one-pot, and three-component protocol has been reported for the stereoselective synthesis of a new class of spiro thiazolidines. A series of spiro-heterocycle derivatives were produced stereoselectively in high yields by the reaction of 5-arylidene thiazolidine-2,4-diones, isatin, and secondary amino acids in the presence of MnCoCuFe2O4@l-proline (MCCFe2O4@l-proline) magnetic nanorods as a novel nanocatalyst. The synthesized catalyst was fully characterized for thermal stability, magnetic properties, and other physicochemical properties via numerous techniques. It was applied as an efficient and reusable catalyst for the synthesis of endo-isomers of spirocyclic pyrrolidine/pyrrolizidine/pyrrolothiazolidine derivatives in high yield. The regioselectivity and stereochemistry of these heterocyclic spiro-compounds were established by 1H, 13C, HMBC, HSQC, and COSY NMR spectroscopy techniques. The main attractive characteristics of the presented protocol are high yield, high level of diastereoselectivity, and easy recovery of catalyst without significant loss of its catalytic activity. This journal is
- Akhavan, Malihe,Bekhradnia, Ahmadreza
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- Biological Prediction from Computational Approach, Synthesis, and Biological Evaluations of Newer Thiazolidine-2,4-dione Conjugates
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Thiazolidine-2,4-dione is a toxophoric unit and its derivatives act as antimicrobial and antitubercular agents. Computational approach two-dimensional quantitative structure-activity relationship (2D-QSAR) was used to predict antitubercular activity of the thizolidine-2,4-dione derivatives. 2D-QSARS generated model using partial least squares regression method which predicted the statistically significant r2 = 0.3868, q2= 0.0193, pred_r2 = 0.5240, and F test = 3.7855. 2D-QSAR model equation denoted log(1/MIC) of the antitubercular activity correlated with thermodynamic descriptor SAMost Hydrophobic Hydrophilic Distance. Biological predicted derivatives of thiazolidine-2,4-dione (Z)-N-(2-(2,4-dichlorophenoxy)phenyl)-2-(5-substitutidene-2,4-dioxothiazolidin-3-yl)acetamide (C1-C10) were synthesized and spectrally evicted from IR, 1H NMR, 13C NMR and Mass spectral data analysis as well as biologically evaluated against antitubercular and antimicrobial activities. From the biologically evaluated derivatives, compounds C1, C2, C3 and C6 were found to be active against the different antimicrobial species. Compounds C1, C3 and C10 are more progressive than others against antitubercular species.
- Patel, Jaydeep A.,Patel, Navin B.,Tople, Manesh S.
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p. 379 - 387
(2021/11/22)
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- Structure guided design and synthesis of furyl thiazolidinedione derivatives as inhibitors of GLUT 1 and GLUT 4, and evaluation of their anti-leukemic potential
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Cancer cells increase their glucose uptake and glycolytic activity to meet the high energy requirements of proliferation. Glucose transporters (GLUTs), which facilitate the transport of glucose and related hexoses across the cell membrane, play a vital ro
- Aguilera, Renato J.,Choe, Jun-yong,Hess, Jessica D.,Iancu, Cristina V.,Macias, Lucasantiago Henze,Meyer-Almes, Franz-Josef,Mrowka, Piotr,Ramaa, C. S.,Tilekar, Kalpana,Upadhyay, Neha
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- Microwave assisted urea-acetic acid catalyzed knoevenagel condensation of ethyl cyanoacetate and 1,3-Thiazolidine-2,4-dione with aromatic aldehydes under solvent free condition
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Knoevengel condensation reaction of various aromatic aldehydes with ethyl cyanoacetate and 1,3-thiazolidinone-2,4-diones catalyzed by urea-acetic acid under solvent free condition where olefinic products were obtained in high yield within short reaction time.
- Tryambake, Pravin. T.
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p. 2401 - 2405
(2017/10/31)
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- Composition for Distructing Microalgae
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The present invention relates to a composition for disrupting microalgae. The composition for disrupting microalgae can suppress growth and proliferation of microalgae when treated in marine microalgae culture farms, areas where green or red tide takes pl
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Paragraph 0137-0142
(2017/04/12)
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- Urea/thiourea catalyzed, solvent-free synthesis of 5-arylidenethiazolidine- 2,4-diones and 5-arylidene-2-thioxothiazolidin-4-ones
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An efficient and organo-catalyzed method has been developed for the synthesis of 5-arylidenethiazolidine-2,4-diones and 5-arylidene-2- thioxothiazolidin-4-ones via Knoevenagel condensation of arylaldehydes 1 and 2,4-thiazolidinedione 2a/2-thioxothiazolidin-4-one 2b under mild conditions. Urea-adduct 4 and azomethine 5 also afford arylidene-products 3 by reacting with 2a-b via addition-elimination reaction. This protocol has the features of use of inexpensive, ecofriendly readily available, effective catalyst system viz. urea/thiourea, avoidance of volatile solvents, excellent yield and simple work-up procedure.
- Shah, Sakshi,Singh, Baldev
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experimental part
p. 5388 - 5391
(2012/09/22)
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- A synthesis of phosphorylated 2,4-dioxothiazolidine derivatives
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The zwitterionic 1:1 intermediates generated from trialkyl phosphites and dialkyl acetylenedicarboxylates are trapped by 2,4-thiazolidinedione and 5-arylidene-2,4-thiazolidinediones to produce dialkyl 2-(2,4-dioxothiazolidin-3- yl)-3-(dialkoxyphosphoryl)
- Yavari, Issa,Sanaeishoar, Tayebeh,Piltan, Mohammad,Azad, Leila
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body text
p. 1612 - 1619
(2011/10/02)
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- Ternary condensation of Biginelli thiones, chloroacetic acid, and aldehydes as an effective approach towards thiazolo[3,2-a] pyrimidines and 5-arylidenethiazolidine-2,4-diones
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(Chemical Equation Presented) At the process of ethyl 6-methyl-4-aryl-2- thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates condensation with aryl aldehydes and chloroacetic acid the unexpected formation of 5- arylidenethiazolidine-2,4-diones was determined in high yields as the reaction time was increased to 20 h. The latter represent the products of destructive hydrolyzes of ethyl 2-benzylidene-7-methyl-3-oxo-5-aryl-2,3-dihydro-5H-[1,3] thiazolo[3,2-a]pyrimidine-6-carboxylates which have been proved by independent synthesis.
- Lebedyeva, Iryna O.,Povstyanoy, Mykhaylo V.,Ryabitskii, Aleksey B.,Povstyanoy, Vyacheslav M.
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scheme or table
p. 368 - 372
(2010/06/14)
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