ChemInform Abstract: Studies on Thiazolidinones as Potential Antitubercular Compounds.

Dave, M. P.; Patel, J. M.; Langalia, N. A.; Thaker, K. A.

doi:10.1002/chin.198702182

Cited by 6 publications

(7 citation statements)

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“…As shown in Table 1, triamino-substituted C 3 -symmetrical derivatives (2a, 19) 2b, and 2d) were obtained predominantly in good yields from reactions of TCTAZ (1) with the corresponding amine nucleophile (Entries 1-3).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Biological Evaluation of Symmetrical 2,4,6-Trisubstituted 1,3,5-Triazine Derivatives

et al. 2013

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We describe the synthesis and biological evaluation of newly designed 2,4,6-trisubstituted symmetrical 1,3,5-triazine (TAZ) derivatives. Among the tested trisubstituted symmetrical TAZ derivatives, various C 3 -or C S -symmetrical alkoxy-amino-substituted TAZ derivatives showed significant antiviral activity against herpes simplex virus type 1 (HSV-1) and/or cytotoxic activity against Vero cells. The structure-activity relationships for anti-HSV-1 activity of these symmetrical 2,4,6-trisubstituted TAZ derivatives are also described. Experimental results indicated that a C S -symmetrical TAZ structure with introduction of two alkoxy groups and one amine moiety seems to be the minimally required structure for anti-HSV-1 activity.Key words 1,3,5-triazine; anti-herpes simplex virus type 1; cytotoxic activity; C 3 symmetry; C S symmetry; plaque reduction assay Molecular recognition of two-fold (C 2 ) or three-fold (C 3 ) symmetrical geometry macromolecules is one of the common features in many important biological responses, 1,2) and we have therefore already designed a few symmetrical target molecules for the purpose of finding biologically active new leads or candidates.3-5) With reference to the molecular symmetry, small molecules having C 3 -, C S -, or C 2 -symmetrical geometry frequently appear in various biologically active compounds. [6][7][8] Such small symmetrical molecules are usually constructed on a corresponding symmetrical template.From this point of view, we have recently reported some molecular modifications of tris(2-aminoethyl) amine (TAEA) derivatives to C 3 -or C S -symmetrical tripodal receptor type molecules and the results of biological evaluation of these symmetrical compounds.3) We have also reported an interesting lectin-like property for sugar recognition of some of these tripodal receptor type TAEA molecules. 4)In order to achieve a suprafacial three-dimensional interaction of a bioactive symmetrical molecule for its binding site, the nature of substituents in the molecule is thought to be very important for preferential interactions. Such interactions are dictated largely by van der Waals interactions or formation of hydrogen bonds. The introduction of amine (basic nitrogen atom) and/or a bivalent oxygen group such as a hydroxy or alkoxy group into a C 3 -symmetrical 1,3,5-triazine (TAZ) template seems to be interesting, because it is well known that amine functionalities behave as both hydrogen acceptors and hydrogen donors in appropriate circumstances. These facts may indicate that molecules with some amine and/or bivalent oxygen functionalities on a heterocyclic C 3 -symmetrical TAZ template can produce a property for suprafacial hydrogenbonding interaction.For an extension of our studies, we planned to investigate the synthesis of 2,4,6-trisubstituted symmetrical TAZ derivatives [9][10][11][12][13][14][15][16] as well as to evaluate their biological properties. In this paper, we report the results of new synthetic routes for C 3 -or C S -symmetrical 2,4,6-trisubstituted TAZ derivativ...

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Section: Resultsmentioning

confidence: 99%

“…Purification by recrystallization from i-PrOH gave an analytically pure product 2a (3.06 g, 54% yield) as colorless crystals: mp 222-225°C (from i-PrOH) [lit. 19) …”

Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Evaluation of Symmetrical 2,4,6-Trisubstituted 1,3,5-Triazine Derivatives

et al. 2013

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“…1), an important chiral multifunctional intermediate in organic synthesis, has been employed widely in the synthesis of various biologically active sulfurs [1], such as antimicrobial [2] and antitubercular [3]. More recently, mercaptosuccinic acid has been used as a building block in the synthesis of novel polyanionic inhibitors of HIV and other viruses [4], and as a starting material in the synthesis of isocysteine, an important nonproteinogenic amino acid present in a potent peptide inhibitor of struiomelysin [5].…”

Section: Introductionmentioning

confidence: 99%

The solubility of mercaptosuccinic acid in water+ (methanol, ethanol, acetone) mixtures from (278.15 to 333.15K)

Kai

Liu

et al. 2014

Fluid Phase Equilibria

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“…It is also used as a building block in the synthesis of novel polyanionic inhibitors of human immunodeficiency virus and other viruses [2], and as a starting material in the synthesis of isocysteine, an important non-proteinogenic aminoacid in a potent peptide inhibitor of stromelysin [3]. In addition, sodium salt of the anionic Au (I) complex of 2-mercaptosuccinic acid is an effective anti-arthritic drug [4][5][6][7][8][9]. MSA is widely applied in industry and technology as corrosion inhibitor, electrolyte for electroplating bath, and components of bleach-fixing baths for photographic films and as an active material for depilatories and hair strengthening [10].…”

Section: …………………………………………………………………………………………………… Introduction:-mentioning

confidence: 99%

Influence of Dielectric Constant on Protonation Equilibria of Mercaptosuccinic Acid, L-Dopa and 1, 10-Phenanthroline in Aqueous Solutions of Dimethylformamide.

AdityaDeepthi¹,

Prasanthi²,

G³

2017

IJAR

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The protonation constant values of mercaptosuccinic acid, L-dopa and 1, 10 -phenanthroline were determined in dimethylformamide (0-60%v/v) at 303.0 K at ionic strength of 0.16 mol L -1 using pH-metric technique. The protonation constants were calculated with the computer program MINIQUAD75 and selection of the best fit models was based on the statistical parameters. The log K values were found to increase of the organic solvent content. The linear variations of the protonation constants with the reciprocal of the dielectric constant of the medium have been attributed to the dominance of electrostatic forces. Distribution of species, protonation equilibria and effect of influential parameters on the protonation constants have also been presented.

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ChemInform Abstract: Studies on Thiazolidinones as Potential Antitubercular Compounds.

Abstract: Das Benzoesäurehydrazid (I) liefert mit den Benzaldehyden (II) die Acylhydrazone (III), an die sich die α‐Mercaptocarbonsäuren (IV) zu den Thiazolidinonen (V) addieren.

Cited by 6 publications

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Synthesis and Biological Evaluation of Symmetrical 2,4,6-Trisubstituted 1,3,5-Triazine Derivatives

Synthesis and Biological Evaluation of Symmetrical 2,4,6-Trisubstituted 1,3,5-Triazine Derivatives

The solubility of mercaptosuccinic acid in water+ (methanol, ethanol, acetone) mixtures from (278.15 to 333.15K)

Influence of Dielectric Constant on Protonation Equilibria of Mercaptosuccinic Acid, L-Dopa and 1, 10-Phenanthroline in Aqueous Solutions of Dimethylformamide.

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