• Journal of the Korean Chemical Society
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• v.51 no.3
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• pp.244-250
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• 2007

A series of new 6-allylthio-3-aminopyridazine derivatives was synthesized through allylthiolation, amination and expected for anti-tumor activity. The pyridazine nucleus was obtained by condensing hydrazine monohydrate with maleic anhydride. 3,6-Dichloropyridazine was synthesized from 3,6-dihydroxypyridazine by treating with POCl3. 6-Allylthio-3-chloropyridazine was prepared from the reaction of 3,6-dichloropyridazine with allylmercaptan and sodium hydroxide. The heterocycles with nitrogen nucleophile such as morpholine, piperazine, pyrazole, imidazole, pyrrolidine, piperidine, perhydroazepine, and perhydroazocine were introduced into 3-position of pyridazine ring. The substitution reaction of 6-allylthio-3-chloropyridazine with heteroamines was performed by refluxing for 24~48 h in n-buthanol with NH4Cl.

• Bulletin of the Korean Chemical Society
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• v.31 no.11
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• pp.3265-3271
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• 2010

A series of 6,7,8,9-tetrahydro-5H-5-hydroxyphenyl-2-benzylidine-3-substituted hydrazino thiazolo (2,3-b) quinazolines have been synthesized to meet the structural requirements essential for anti-inflammatory and antinociceptive properties. The synthesized series of heterocycles, 6,7,8,9-tetrahydro-5H-5-hydroxyphenyl-2-benzylidine-3-substituted hydrazino thiazolo (2,3-b) quinazoline by the reaction of 6,7,8,9-tetrahydro-5H-5-hydroxy phenyl thiazolo (2,3-b) quinazolin-3(2H)-one with appropriate hydrazine hydrate and ketones/aldehydes in the presence of anhydrous sodium acetate and glacial acetic acid as presented in Scheme 1. Their antinociceptive activity were evaluated by tailflick technique, anti-inflammatory was evaluated by carrageenan-induced paw edema test and their ulcerogenicity index determined by reported protocol. The compounds exhibited the lowest ulcer index ($0.51{\pm}1.63$, $0.48{\pm}1.28$ and $0.50{\pm}1.53$, respectively. The 6,7,8,9-tetrahydro-5H-5-hydroxy phenylhydroxy-2-benzylidine-3-(N'-3-pentylidenehydrazino) thiazolo (2,3-b) quinazoline and 6,7,8,9-tetrahydro-5H-5-hydroxy phenyl-2-benzylidine-3-(N'-2-pentylidene-hydrazino) thiazolo (2,3-b) quinazoline exhibited the most potent antinociceptive and anti-inflammatory activities.

• Journal of the Korean Chemical Society
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• v.40 no.7
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• pp.526-530
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• 1996

3-(N-Alkylamino)-4,5-dihydro-1,2,5-thiadiazole 1,1-dioxides have been prepared by the treatment of 3-imino-1,2,5-thiadiazolidine 1,1-dioxides with alkylamines. The selected spectral properties of these heterocycles are detailed, as well as an X-ray crystallographic structure of a representative member of these compounds. 3-(N-Benzylamino)-4,5-dihydro-4-(4'-methoxyphenyl)-1,2,5-thiadiazole 1,1-dioxide crystallyzes in space group $P2_1a$, monoclinic, with $a=22.512(3)(1)\AA$, $b=9.831(2)\AA$, $c=7.194(4)\AA$, $\beta=96.65(2)$, and Z=4.