Antidermatophytic Activity of 2‐Thiotetrahydro‐1,3,5‐thiadiazines and Isothiocyanates

Manohar, Vijaya; Murthy, Sridhara; Sirsi, M; Rao, G. Ramananda; Rao, P. Krishna

doi:10.1002/jps.2600640140

Cited by 4 publications

(3 citation statements)

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“…In summary, the reactivity of thiobarbituric acid as a versatile and readily accessible building block for the synthesis of new 3,4-dihydropyrimido[2,1-b] [1,3,5]thiadiazine-6,8-(2H,7H)dione and [1,2,4]triazolo [4,3-a]pyrimidine-5,7-(1H,6H)-dione derivatives was studied. The new compounds were tested for their aromatase inhibition activity.…”

Section: Discussionmentioning

confidence: 99%

“…1 32 were prepared as described in the literature. [1,3,5]thiadiazine-6,8-(2H,7H)-dione derivatives 3a-g; general procedure A mixture of thione 1 (0.144g, 1 mmol), 37% formaldehyde (2 mL) and the appropriate aromatic amine derivative (2a-g) (1 mmol) in dioxane (20 mL) in presence of a few drops of HCl (6M) was stirred at room temperature for 4-10 h (monitored by TLC). The solids that precipitated were filtered off, washed with water, dried and finally crystallised from dioxane to give pure 3a-g respectively.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of New Functionalised Derivatives of [1,2,4]triazolo[4,3-a]Pyrimidine and Pyrimido[2,1-b][1,3,5]Thiadiazine as Aromatase Inhibitors

Gomha

Abdelrazek

Abdulla³

2015

Journal of Chemical Research

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Thiadiazines are class of heterocyclic compounds that posses antimicrobial, 1-7 tuberculostatic, 8 antiprotozoan, 9 antihelmintic, 2 antifibrinolytic 7 and anticancer 10 activities. Fused derivatives of 1,3,5-thiadiazine are most suitably synthesised by a Mannich-type condensation of mercaptoazoles with formaldehyde and primary amines. 11,12 The [1,2,4]-triazolopyrimidines are pharmacological scaffolds displaying a wide range of biological activities such as antitumour, 13 human A3 adenosine receptor, 14 antimicrobial, 15,16 antiallergy 17 and 5a-reductase inhibitors. 18 In continuation of our efforts [19][20][21][22][23][24] to synthesise new heterocyclic compounds that may have potent biological activities, we decided to synthesise new triazolopyrimidines and pyrimidothiadiazines and to investigate their activity as aromatase inhibitors compared with the drug letrozole. Results and discussionThiobarbituric acid 1 was prepared as previously reported. 25 Reaction of thione 1 with different primary aromatic amines, aqueous formaldehyde solution and catalytic amounts of concentrated HCl in ethanol at room temperature, afforded in each case, only one product, as examined by TLC, which was identified as the respective pyrimidothiadiazinones 3a-g through the di-Mannich reaction (Scheme 1). The structures of compounds 3a-g were confirmed by spectroscopic data and elemental analyses. For instance, the IR spectra of compounds 3a-g were devoid of absorption bands at 3400-3100 cm -1 characteristic for 2NH functions. The 1 H NMR spectrum of compound 3a, taken as a typical example, showed two peaks for the methylene protons of the 1,3,5-thiadiazine rings at δ 5.44 and 5.96, two singlets attributed to the methine protons at 6.74 and 6.76 ppm, in addition to an aromatic multiplet in the region 6.94-7.32 ppm. The mass spectrum of compound 3a revealed the molecular ion peak at m/z 261.The thione 1 reacts with the hydrazonoyl chlorides 4a-k dioxane in the presence of a catalytic amount of triethylamine while stirring at room temperature. In all cases, hydrogen sulfide was evolved during the course of the reaction and so the stirring of the reaction mixture was continued until hydrogen sulfide ceased to evolve. Work-up of the reaction mixture afforded, in each case, one isolable product as evidenced by TLC analysis of the crude product. The structures of the products were assigned on the basis of their elemental analyses and IR and 1 H NMR spectra which showed all the expected signals (see Experimental).The formation of compounds 8 from 1 and 4 could be accounted for by the hydrazonoylation of 1 to give the thiohydrazonate esters 5, which is followed by Smiles type rearrangement 26 to afford the respective thiohydrazides 6. This latter compound 6, in turn, underwent cyclisation to give 8 as the end products (Scheme 2). It seems likely that both intermediates 5 and 6 are consumed, under the employed reaction conditions, as soon as they are formed since all attempts to isolate them failed.Thione 1 (2 equiv.) were allowed to react wi...

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Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Synthesis of New Functionalised Derivatives of [1,2,4]triazolo[4,3-a]Pyrimidine and Pyrimido[2,1-b][1,3,5]Thiadiazine as Aromatase Inhibitors

Gomha

Abdelrazek

Abdulla³

2015

Journal of Chemical Research

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“…1,3,5-Thiadiazines have attracted considerable attention over the years because of their biological activities and applications in medicine and agriculture (for reviews on the 1,3,5-thiadiazine chemistry, see refs − ). 1,3,5-Thiadiazines are known as antidermatophites, , antifungal and fungistatic agents, − antimicrobials and bactericides, − antifibrinolytic agents, − tuberculostatics, − etc. Thiadiazines are widely used as insecticides .…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Pyrido[2,1-b][1,3,5]thiadiazine Library via Uncatalyzed Mannich-Type Reaction

Dotsenko

Фролов

Pekhtereva³

et al. 2014

ACS Comb. Sci.

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This Research Article describes the synthesis of an over 700-member library of (8R/8S)-3-R-8-aryl-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazin-9-carbonitriles by uncatalyzed Mannich-type reaction of N-methylmorpholinium (4R/4S)-4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridin-2-thiolates with a set of primary amines and excessive HCHO. The scope and limitations of the reaction were studied. Starting thiolates were obtained in yields of 53-82% by multicomponent reaction of aromatic aldehydes, cyanothioacetamide, 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid), and N-methylmorpholine, followed by heterocyclization of the resulting Michael adducts.

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Antifungal agents

D’Arcy

Scott

1978

Progress in Drug Research / Fortschritte Der Arzneimittelforschung / Progrès Des Recherches Pharmaceutiques

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Antidermatophytic Activity of 2‐Thiotetrahydro‐1,3,5‐thiadiazines and Isothiocyanates

Cited by 4 publications

References 3 publications

Synthesis of New Functionalised Derivatives of [1,2,4]triazolo[4,3-a]Pyrimidine and Pyrimido[2,1-b][1,3,5]Thiadiazine as Aromatase Inhibitors

Synthesis of New Functionalised Derivatives of [1,2,4]triazolo[4,3-a]Pyrimidine and Pyrimido[2,1-b][1,3,5]Thiadiazine as Aromatase Inhibitors

Design and Synthesis of Pyrido[2,1-b][1,3,5]thiadiazine Library via Uncatalyzed Mannich-Type Reaction

Antifungal agents

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