Crystal structure, computational studies, and stereoselectivity in the synthesis of 2-aryl-thiazolidine-4-carboxylic acids via <i>in situ</i> imine intermediate

Jagtap, Rohidas M.; Rizvi, Masood Ahmad; Dangat, Yuvraj; Pardeshi, Satish K.

doi:10.1080/17415993.2016.1156116

Cited by 14 publications

(7 citation statements)

References 39 publications

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“…It is worth mentioning that using acidified methanol gave a better yield and an opposite diastereomeric ratio compared to the previously reported results 39 (Table, entry a). This result encouraged us to study the diastereoselectivity in the formation of 2-(substituted)thiazolidine-4-carboxylic acids by using our conditions.…”

Section: Resultscontrasting

confidence: 43%

“…[39][40][41][42][43] It seems that using our optimal conditions in the synthesis of 2-(substituted)thiazolidine-4-carboxylic acids affects both the experimental yield and diastereomeric ratio (Table). Thus, using such conditions afforded diastereomeric mixtures of 7 and 8 in 75-98% yields, and the cis-diastereomer 7 was obtained as the major product in all cases.…”

Section: Scheme 3 Synthesis Of 35-bis(2-nitrophenyl)tetrahydro-1h-tmentioning

confidence: 99%

“…The reaction was carried out according to general procedure (method A) using 3-nitrobenzaldehyde 2g as a carbonyl component and heating for 8h. An isomeric mixture of 7g and 8g was obtained in a 2:1 ratio, respectively, (2.34 g, 92%) (Lit., 80%) 39 (3S,7aR)-3-(3-Nitrophenyl)-6-phenyl-5-thioxotetrahydroimidazo[1,5-c]thiazol-7(3H)-one (12g). The reaction was carried out according to the general procedure (method B) using thiazolidines 7g and 8g.…”

Section: (2rs4r)-2-(2-hydroxyphenyl)thiazolidine-4-carboxylic Acid (mentioning

confidence: 99%

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New aspects of the formation of 2-substituted thiazolidine-4-carboxylic acids and their thiohydantoin derivatives

Mahdy¹,

Elboray²,

Fandy³

et al. 2017

Arkivoc

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Aromatic aldehydes reacted readily with (R)-cysteine in boiling acidified methanol to give diastereomeric mixtures of the corresponding 2-(aryl substituted) thiazolidine-4-carboxylic acids. 4-Nitrobenzaldehyde under similar conditions afforded one isomer of 2-(4-nitrophenyl)-thiazolidine-4-carboxylic acid, which epimerized in the NMR solvents into a diastereomeric mixture. 2-Nitrobenzaldehyde reacted with (R)-cysteine to afford 3,5-bis-(2-nitrophenyl)-tetrahydro-1H-thiazolo[3,4-c]oxazol-1-one as the sole product, which collapsed in the NMR solvent into a diastereomeric mixture of the thiazolidine-4-carboxylic acids. The thiazolidine derivatives reacted smoothly with phenyl isothiocyanate to give single isomers of the corresponding thiohydantoins.

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Section: Resultscontrasting

confidence: 43%

Section: Scheme 3 Synthesis Of 35-bis(2-nitrophenyl)tetrahydro-1h-tmentioning

confidence: 99%

Section: (2rs4r)-2-(2-hydroxyphenyl)thiazolidine-4-carboxylic Acid (mentioning

confidence: 99%

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New aspects of the formation of 2-substituted thiazolidine-4-carboxylic acids and their thiohydantoin derivatives

Mahdy¹,

Elboray²,

Fandy³

et al. 2017

Arkivoc

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“…The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbitals (LUMO) energies of bikaverin (1) and all its metal ion adducts have been summarized in (Table S1, see supporting information).The interactions between the metal ions and the bikaverin (1) can be clearly observed from the frontier molecular orbital contour distribution. 33 In case of bikaverin (1), the HOMO and LUMO are spread evenly over the benzoquinone and hydroquinone rings of the molecule. The observed changes in the HOMO and LUMO contours of bikaverin (1) indicate a pi to pi* transition in absorption.…”

Section: Resultsmentioning

confidence: 99%

Exploring Bikaverin as Metal Ion Biosensor: A Computational Approach

Hussain

Bhat

Naqvi³

et al. 2019

ACSi

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A computational exploration of fungi produced pigment bikaverin as a biosensor towards bioavailable metal ions is presented. Systematic studies of the optimized ground and excited state geometries were attempted for exploring metal ion binding pocket, comparative binding propensity and optical properties of the bikaverin and its adducts with studied metal ions. The screening of thirteen (13) bioavailable metal ions, revealed a range of binding strength towards bikaverin receptor with Ca 2+ , Mg 2+ and Al 3+ as the strongest binders. Besides, upon binding to bikaverin receptor an enhancement in its fluorescence intensity was observed in the order Ca 2+ > Al 3+ > Mg 2+ . The computationally predicted selectivity of bikaverin receptor towards Ca 2+ was experimentally corroborated through the preliminary fluorescence studies. The bikaverin probe showed an enhancement of fluorescence emission in presence of Ca 2+ ions in buffered aqueous medium.

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“…In our earlier research work on ATCAs, it has been found that the thiazolidine ring is prone to ring opening tautomerism in presence of acidic conditions, high temperature reactions and polar medium . Thus, the synthesis of their anilides is practicable at only mild conditions using a suitable coupling agent which can work without any additive and offers fair purity of the products.…”

Section: Introductionmentioning

confidence: 99%

Cyanuric‐Chloride‐Mediated Synthesis of 2‐Aryl‐3‐tert‐butoxycarbonyl‐thiazolidine‐4‐carboxylic Acid Anilides: Mechanistic, X‐Ray Crystal Structures and Cytotoxicity Studies

et al. 2019

Self Cite

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The ‘2R,4R’‐2‐aryl thiazolidine‐4‐carboxylic acid anilides (ATCAAs) were synthesized using cyanuric chloride (CC) as a clean and substoichiometric acid‐amine coupling agent under optimized reaction conditions. The diesterphenol intermediate based mechanism is proposed and supported by spectral characterization of the intermediate. The single crystal X‐ray structures of acid substrate (2R,4R)‐3‐(tert‐butoxycarbonyl)‐2‐(2‐methoxyphenyl)thiazolidine‐4‐carboxylic acid (3 a) and anilides (R)‐tert‐butyl 4‐(2‐fluorophenylcarbamoyl)thiazolidine‐3‐carboxylate (4 b), (2R,4R)‐tert‐butyl 2‐(2,6‐dichlorophenyl)‐4‐(m‐tolylcarbamoyl)thiazolidine‐3‐carboxylate (6 b) confirmed the formation of chiral anilides. The synthesized library of anilides [(R)‐tert‐butyl 4‐Aryl thiazolidine‐3‐carboxylate and (2R,4R)‐tert‐butyl 2‐Aryl‐4‐Aryl thiazolidine‐3‐carboxylate] 4 a‐6 f was screened for their in vitro anti cancer, neuronal and neuroprotective studies. The anilides 4 b, 4 g, 5 d, 5 h, 6 c and 6 f (where the aryl=2‐fluorophenylcarbamoyl, 4‐chlorophenylcarbamoyl, 2‐methoxyphenyl, 2,5‐dichlorophenylcarbamoyl, 2,6‐dichlorophenyl, 4‐chlorophenylcarbamoyl respectively)were found to be less cytotoxic towards N2 A, SHSY‐5Y neuronal cell lines in their differentiated and undifferentiated forms, and also exhibited dose dependant anti‐inflammatory properties for a possible identification towards neurodegenerative and inflammatory disorders.

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Crystal structure, computational studies, and stereoselectivity in the synthesis of 2-aryl-thiazolidine-4-carboxylic acids via in situ imine intermediate

Cited by 14 publications

References 39 publications

New aspects of the formation of 2-substituted thiazolidine-4-carboxylic acids and their thiohydantoin derivatives

New aspects of the formation of 2-substituted thiazolidine-4-carboxylic acids and their thiohydantoin derivatives

Exploring Bikaverin as Metal Ion Biosensor: A Computational Approach

Cyanuric‐Chloride‐Mediated Synthesis of 2‐Aryl‐3‐tert‐butoxycarbonyl‐thiazolidine‐4‐carboxylic Acid Anilides: Mechanistic, X‐Ray Crystal Structures and Cytotoxicity Studies

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