2-Substituted-thiazolidine-4-carboxylic Acids

Soloway, Harold; Kipnis, Frank; Ornfelt, John; Spoerri, Paul E.

doi:10.1021/ja01184a520

Cited by 34 publications

(16 citation statements)

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“…Thiazolidine [11] 7, 1-butenyl-thiazolidine 9, 1H,3H-pyrrolo[1,2-c]thiazole 10, and 2,2-dioxo-7-(trifluoromethyl)-1H,3H-pyrrolo[1,2-c]thiazole 4d were prepared by modifying a procedure described in the literature. The reaction temperatures were measured by infrared surface detector during microwave heating.…”

Section: Methodsmentioning

confidence: 99%

“…The reaction temperatures were measured by infrared surface detector during microwave heating. Thiazolidine [11] 7, 1-butenyl-thiazolidine 9, 1H,3H-pyrrolo[1,2-c]thiazole 10, and 2,2-dioxo-7-(trifluoromethyl)-1H,3H-pyrrolo[1,2-c]thiazole 4d were prepared by modifying a procedure described in the literature. [5] 19 F NMR spectra were recorded with an instrument operating at 376 MHz.…”

Section: Methodsmentioning

confidence: 99%

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1‐Methyl‐5‐(trifluoromethyl)azafulvenium Methide, an Intermediate That Undergoes Reaction through “Unusual” cis‐exo‐1,3‐ and trans‐exo‐1,7‐Cycloadditions

Peláez¹,

Pepino²,

Argüello³

et al. 2014

Eur J Org Chem

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The generation and reactivity of a new 1‐methyl‐5‐(trifluoromethyl)azafulvenium methide are described. Under microwave‐induced pyrolysis conditions this intermediate could be trapped by dipolarophiles, acting either as a 4π or as an 8π dipole. Quantum chemical calculations carried out at the DFT level of theory allowed the rationalization of the results observed in the cycloaddition of 1‐methyl‐5‐(trifluoromethyl)azafulvenium methide and N‐substituted maleimides. The study revealed that for 1,7‐cycloadducts the major products are obtained in the trans configuration through the unusual exo‐cycloaddition mode, whereas for 1,3‐cycloadducts the cis counterparts are obtained from this unexpected approach. In addition, under flash vacuum pyrolysis or conventional thermolysis conditions 1‐methyl‐5‐(trifluoromethyl)azafulvenium methide undergoes an allowed suprafacial sigmatropic [1,8]H shift leading to the formation of 2‐methyl‐3‐(trifluoromethyl)‐1‐vinyl‐1H‐pyrrole.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

1‐Methyl‐5‐(trifluoromethyl)azafulvenium Methide, an Intermediate That Undergoes Reaction through “Unusual” cis‐exo‐1,3‐ and trans‐exo‐1,7‐Cycloadditions

Peláez¹,

Pepino²,

Argüello³

et al. 2014

Eur J Org Chem

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“…161–164 °C (lit. [ 35 ] 167–1169 °C); 1 H-NMR (DMSO- d 6 ): 9.51 (br s, 1H, O H ), 7.33 (d, J = 8.8 Hz, 1H, Ar- H ), 7.26 (d, J = 8.0 Hz, 1H, Ar- H ), 6.75 (d, J = 8.0 Hz, 1H, Ar- H ), 6.72 (d, J = 8.8 Hz, 1H, Ar- H ), 5.55 (s, 0.5H, Ar-C H ), 5.41 (s, 0.5H, Ar-C H ), 4.26 (dd, J = 3.6 and 6.8 Hz, 0.5H, CH 2 C H ), 3.86 (t, J = 7.6 Hz, 0.5H, CH 2 C H ), 3.36 (dd, J = 6.8 and 10.0 Hz, 0.5H, C H 2 ), 3.28 (dd, J = 6.8 and 10.0 Hz, 0.5H, C H 2 ), 3.16 (dd, J = 3.6 and 10.4 Hz, 0.5H, C H 2 ), 3.06 (t, J = 9.2 Hz, 0.5H, C H 2 ); 13 C-NMR (DMSO- d 6 ): 173.1, 172.3, 157.4, 156.9, 130.7, 128.8, 128.5, 128.3, 115.1, 114.9, 71.8, 71.2, 65.2, 64.7, 38.5, 37.8; HRMS (ESI) m/z calc’d for C 10 H 11 NO 3 S [M + H] + : 225.0460, found 225.0463.…”

Section: Methodsmentioning

confidence: 99%

“…152–155 °C (lit. [ 35 ] 165–166 °C); 1 H-NMR (DMSO- d 6 ): 7.18–7.30 (m, 5H, Ar- H ), 4.81 (t, J = 7.0 Hz, 0.7H, SC H ), 4.65 (t, J = 6.8 Hz, 0.3H, SC H ), 4.15 (dd, J = 5.6 and 6.7 Hz, 0.7H, CH 2 C H ), 3.72 (dd, J = 6.9 and 9.2 Hz, 0.3H, CH 2 C H ), 3.07–3.27 (m, 2H, CH 2 C H and Ar- CH 2 ), 3.00 (dd, J = 7.3 and 13.7 Hz, 0.3H, CH 2 C H ), 2.92 (dd, J = 5.4 and 10.2 Hz, 0.7H, CH 2 C H ), 2.75–2.85 (m, 1H, Ar- CH 2 ); 13 C-NMR (DMSO- d 6 ): 173.3, 172.7, 139.5, 139.3, 129.6, 129.4, 128.7, 128.6, 126.9, 126.7, 72.4, 71.8, 65.7, 64.6, 43.3, 41.1, 37.8, 37.6; HRMS (ESI) m/z calc’d for C 11 H 13 NO 2 S [M + H] + : 223.0667, found 223.0662.…”

Section: Methodsmentioning

confidence: 99%

Discovery of Cysteine and Its Derivatives as Novel Antiviral and Antifungal Agents

et al. 2021

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Based on the structure of the natural product cysteine, a series of thiazolidine-4-carboxylic acids were designed and synthesized. All target compounds bearing thiazolidine-4-carboxylic acid were characterized by 1H-NMR, 13C-NMR, and HRMS techniques. The antiviral and antifungal activities of cysteine and its derivatives were evaluated in vitro and in vivo. The results of anti-TMV activity revealed that all compounds exhibited moderate to excellent activities against tobacco mosaic virus (TMV) at the concentration of 500 μg/mL. The compounds cysteine (1), 3–4, 7, 10, 13, 20,23, and 24 displayed higher anti-TMV activities than the commercial plant virucide ribavirin (inhibitory rate: 40, 40, and 38% at 500 μg/mL for inactivation, curative, and protection activity in vivo, respectively), especially compound 3 (inhibitory rate: 51%, 47%, and 49% at 500 μg/mL for inactivation, curative, and protection activity in vivo, respectively) with excellent antiviral activity emerged as a new antiviral candidate. Antiviral mechanism research by TEM exhibited that compound 3 could inhibit virus assembly by aggregated the 20S protein disk. Molecular docking results revealed that compound 3 with higher antiviral activities than that of compound 24 did show stronger interaction with TMV CP. Further fungicidal activity tests against 14 kinds of phytopathogenic fungi revealed that these cysteine derivatives displayed broad-spectrum fungicidal activities. Compound 16 exhibited higher antifungal activities against Cercospora arachidicola Hori and Alternaria solani than commercial fungicides carbendazim and chlorothalonil, which emerged as a new candidate for fungicidal research.

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“…The present report describes synthesis, antifungal activity and QSAR studies of the thiazolidine derivatives. ed phenyl) thiazolidine-4-carboxylic acids and their Nacylated products were synthesized in solution phase (Scheme 1) following a reported procedure [12,13]. The thiazolidines carrying the amino acid at the C4-carboxyl of thiazolidine were synthesized on a solid support in two steps (scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and QSAR Studies on the Antifungal Activity of 2,3,4‐Substituted Thiazolidines

Prabhakar¹,

Jain

Khan

et al. 2003

QSAR Comb. Sci.

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2,3,4-Substituted Thiazolidines were synthesized and explored for antifungal activity against Candida albicans, Cryptococcus neoformans, Tricophyton mentagrophyte and Aspergillus fumigatus. The 2D-and 3D-QSAR studies indicate the usefulness of this skeleton as a potential scaffold to explore new antifungal agents. The activity of these compounds against Candida albicans appears to be non-specific. For the remaining three fungal organisms, the 3D-equations identified are based on three biophoric centers. In case of Cryptococcus neoformans and Tricophyton mentagrophyte, both 2D and 3D-QSAR equations have highlighted the positive role of bulk properties of the compounds in deciding their antifungal activity. Among the models, the one against Aspergillus fumigatus is the most complex and identifies thiazolidines C4 and C2-phenyl region as main players in deciding the activity in terms of steric and electronic properties, respectively. All these equations suggest the necessity of steric and hydrophobic groups at C4 substitution and C2-phenyl moiety of thiazolidine for optimum and broad-spectrum antifungal activity. Also, the models suggest that S1, N3, C2-phenyl moiety, oxygen of t-butyloxy carbonyl or benzoyl attached to N3 and carboxyl oxygen of C4 of thiazolidines are the part of most probable centers for biophoric sites.

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2-Substituted-thiazolidine-4-carboxylic Acids

Cited by 34 publications

References 0 publications

1‐Methyl‐5‐(trifluoromethyl)azafulvenium Methide, an Intermediate That Undergoes Reaction through “Unusual” cis‐exo‐1,3‐ and trans‐exo‐1,7‐Cycloadditions

1‐Methyl‐5‐(trifluoromethyl)azafulvenium Methide, an Intermediate That Undergoes Reaction through “Unusual” cis‐exo‐1,3‐ and trans‐exo‐1,7‐Cycloadditions

Discovery of Cysteine and Its Derivatives as Novel Antiviral and Antifungal Agents

Synthesis and QSAR Studies on the Antifungal Activity of 2,3,4‐Substituted Thiazolidines

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