Studies on Chemotherapeutics. II

Asano, Kazuo

doi:10.1248/yakushi1947.78.7_729

Cited by 10 publications

(3 citation statements)

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“…Earlier reports for this type of O/S conversions were achieved by several thiating reagents; for instance, Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide) [ 1 – 3 ], Berzelius reagent [ 4 – 6 ] (P 4 S 10 ), and phosphorus pentasulfide [ 7 ] in dry toluene, xylene or pyridine under reflux conditions. A two-step approach for the purpose of thiation of heterocyclic amides attracted our attention: as a first step, we applied a chlorination of heterocyclic amides, followed by thiation via reaction with thiourea on the basis of reagent-promoted desulfurylation of isothiourea under strong basic conditions [ 8 – 9 ]. Aiming to continue our reseach work on the structure modification of functionalized heterocyclic amides and thioamides [ 10 – 17 ], we found it interesting to design a new convenient and simple method for the thiation of heterocyclic amides.…”

Section: Introductionmentioning

confidence: 99%

A novel method for heterocyclic amide–thioamide transformations

Fathalla¹,

Ali²,

Pazdera³

2017

Beilstein J. Org. Chem.

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In this paper, we introduce a novel and convenient method for the transformation of heterocyclic amides into heteocyclic thioamides. A two-step approach was applied for this transformation: Firstly, we applied a chlorination of the heterocyclic amides to afford the corresponding chloroheterocycles. Secondly, the chloroherocycles and N-cyclohexyl dithiocarbamate cyclohexylammonium salt were heated in chloroform for 12 h at 61 °C to afford heteocyclic thioamides in excellent yields.

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Section: Introductionmentioning

confidence: 99%

A novel method for heterocyclic amide–thioamide transformations

Fathalla¹,

Ali²,

Pazdera³

2017

Beilstein J. Org. Chem.

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“…The transformation of heterocyclic amides into thioamides is an important task in organic synthesis. Earlier reports for this type of O / S conversions were achieved by several thiating reagents such as Lawesson's reagent (2,4‐bis(4‐methoxyphenyl)‐1,3‐dithia‐2,4‐diphosphetane‐2,4‐disulfide) , Berzelius reagent (P 4 S 10 ), and phosphorus pentasulfide in dry toluene, xylene, or pyridine under reflux condition. Thus, the reaction of 2‐arylquinazolin‐4(3 H )‐one 1a – b with phosphorus pentasulfide in boiling xylene afforded 2‐arylquinazolin‐4(3 H )‐thione 4a – b in poor yield 14% (method C), with bad smell during the workup procedure.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Methyl 2‐(2‐(2‐Arylquinazolin‐4‐yl)sulfanyl)acetylamino Alkanoates

Megahed

Fathalla

2018

Journal of Heterocyclic Chem

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A series of methyl 2-(2-(2-arylquinazolin-4-yl)sulfanyl)acetylamino alkanoates have been developed on the basis of the S-chemoselective reaction of 2-arylquinazolin-4(3H)-thione with ethyl chloroacetate and N,N 0 -dicyclohexylcarbodiimide coupling method with amino acid ester hydrochloride. The precursor 2arylquinazolin-4(3H)-thione was prepared by a new thiation method from 2-arylquinazolin-4(3H)-one by a two-step reaction that includes chlorination and then the reaction with N-cyclohexyldithiocarbamate cyclohexyl ammonium salt. The antimicrobial activity of the synthesized compounds was tested in vitro via paper-disc agar-plate method against two bacterial strains Gram-positive bacteria Staphylococcus aureus and Gram-negative bacteria Escherichia coli and a pathogenic yeast Candida albicans. Most synthesized compounds showed remarkable antibacterial activity against E. coli overpassing the standard reference antibiotics applied: tetracycline, erythromycin, and novobiocin. On the other hand, most synthesized compounds gave moderate antifungal activity against pathogenic yeast C. albicans. Scheme 1. Synthesis of 2-((2-arylquinazolin-4-yl)thio)acetic acid 6a-b.

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“…2-Hydrazino-3-methylquinoxaline (2) [23,24] was prepared in good yields by the reaction of the corresponding methyl sulfone with hydrazine hydrate. Compound 2 was allowed to react with LR (1) The structure of compound 3 was confirmed on the basis of its elemental and spectral analysis (cf.…”

Section: Resultsmentioning

confidence: 99%