350-12-9

Basic information

• Product Name: sulbentine
• Synonyms: sulbentine;Dibenzthione;3,5-Dibenzyltetrahydro-2H-1,3,5-thiadiazine-2-thione;D-47;Dibenzthion;3,5-bis(benzyl)-1,3,5-thiadiazinane-2-thione;3,5-bis(phenylmethyl)-1,3,5-thiadiazinane-2-thione;3,5-DIBENZYL-3,4,5,6-TETRAHYDRO-2H-1,3,5-THIADIAZINE-2-THIONE
• CAS NO: 350-12-9
• Molecular Formula: C₁₇H₁₈N₂S₂
• Molecular Weight: 246.39096
• EINECS: 206-497-2
• Product Categories: FUNGIPLEX
• Mol File: 350-12-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 101-102°
• Boiling Point: 451.5°Cat760mmHg
• Flash Point: 226.9°C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 2.42E-08mmHg at 25°C
• Refractive Index: 1.705
• CAS DataBase Reference: sulbentine(CAS DataBase Reference)
• NIST Chemistry Reference: sulbentine(350-12-9)
• EPA Substance Registry System: sulbentine(350-12-9)

Safety Data

• Hazardous Substances Data: 350-12-9(Hazardous Substances Data)

Usage

Uses

antifungal

InChI:InChI=1/C17H18N2S2/c20-17-19(12-16-9-5-2-6-10-16)13-18(14-21-17)11-15-7-3-1-4-8-15/h1-10H,11-14H2

Upstream product

• 50-00-0 formaldehyd 
• 1950-25-0 potassium benzylcarbamodithioate 
• 100-46-9 benzylamine 
• 75-15-0 carbon disulfide 

Downstream Products

• 622-78-6 Benzyl isothiocyanate 

Relevant articles and documents

Synthesis and antimicrobial activities of 2-thione-3-substituted-5-(4-carboxycyclohexyl-methyl)-tetrahydro-2H-1, 3, 5-thiadiazine derivatives

(Formula Presented) In this study, 3-substituted-5-(4-carboxycyclohexyl-methyl)-tetrahydro-2H-1, 3, 5-thiadiazine-2-thione which have phenylethyl (1), octyl (2), cyclopropyl (3), 4-methoxybenzyl (4), phenyl (5) groups in position 3 have been synthesized and examined for antimicrobial activities. Their structures were elucidated by spectral method. Antibacterial activities of these compounds against Gram-positive bacteria (Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212), gram-negative bacteria (Escherichia coli ATCC 2592, Pseudomonas aeruginosa ATCC 27853) and yeast-like fungi (Candida albicans ATCC 10231, Candida parapsilosis ATCC 90018) were investigated by the micro-dilution method and compared with the activity of sulbentine, ciprofloxacin and flucanozole. By this way their minimal inhibitory concentration (MIC) values were determinated. Compounds 1-4 exhibited almost equally potent activity against Staphylococcus aureus ATCC 29213 (MIC: 31.2 μg/mL). Compounds 1, 3, 4 showed similar antibacterial activity against Enterococcus faecalis ATCC 29212) (MIC: 62.5 μg/mL). None of the compounds exhibited activity against Gram-negative bacteria. On the other hand, all compounds had potent antifungal activities against the yeast utilized. Compounds 1-4 displayed significant antifungal activity against Candida parapsilosis ATCC 90018 at 7.8 μg/mL concentration while sulbentine was active at 125 μg/mL. Among the synthesized compounds, 3-cyclopropyl-5-(4-carboxycyclohexyl-methyl)-tetrahydro-2H-1, 3, 5-thiadiazine-2-thione(3) seems to be the most effective compound with antibacterial and antifungal activity.

Model for delivery of amines through incorporation into a tetrahydro-2H-1,3,5-thiadiazine-2-thione structure

Phenethylamine 1a (a; n = 2) and benzylamine 1b (b; n = 1) are known in medicinal chemistry as strong vasopressors.Both are excellent substrates for the enzyme monoamine oxidase (MAO).The 2 compounds were incorporated in a highly lipid-soluble and hydrolysis-vulnerable tetrahydrothiadiazine (THTT) target structure in order to modify their pharmacokinetics.Better partition correlations, expressed as log P (calculated and observed) for the synthesized products THTT in comparison to the original compounds 1a,b have been found.One of the THTT derivatives was tested for its liability for chemical hydrolysis and the structure of the hydrolytic product was determined. tetrahydro-2H-1,3,5-thiadiazine-2-thione / phenethylamine / benzylamine / prodrugs / monoamine oxidase inhibitors / partition coefficient / hydrolysis

New compounds with bactericidal and fungicidal activity and which inhibit the growth of viruses. I. 2-thiotetrahydro-1,3,5-thiadiazine ("carbothialdine") and dithiocarbamic acid salts.

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