• Archives of Pharmacal Research
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• 제13권4호
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• pp.314-318
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• 1990

2-Bromo (2'-benzofury)gloxal-2-aryhydrazones I reacted with nucleophiles displacing the bromide. Treatment of I with active methylene compounds yield the pyrazole derivatives VIII-XI. Compounds XII-XIV reacted with hydrazine to give pyrazolo (3, 4-dipyridazine derivative XIV-XIV. The structures of the products were assigned and confirmed on the basis of their elemental analysis and spectral data.

• 약학회지
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• 제46권3호
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• pp.155-160
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• 2002

Through a modification of allicin structure a disagreeable odor and chemical instability of allicin can be improved. 3-Alkoxy-6-allylthiopyridazine derivatives exhibit a superior effect for prevention and treatment of hepatic diseases induced by carbon tetrachloride and aflatoxin B1 and for prevention of human tissues from radiation. These compounds inhibit also efficiently SK-Hep-1 cell proliferation through induction of apoptosis. So another 4,5-mono- or di-substituted 3-alkyloxy-6-allylthiopyridazine derivatives were synthesized on purpose to find out SAR of allylthiopyridazine in hepatoprotective and hepatotherapeutic acitivitis and to develop more effective drug candidate.

• Archives of Pharmacal Research
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• 제24권3호
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• pp.180-189
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• 2001

A new series of pyridazine, pyrazoles, pyrazolidine-3,5-dione, Semicarbazide, thiosemicarbazides, hydantoin, thiohydantoins, 1,2,4-triazoles, S-triazolo[3,4-b]-1,3,4-thiadiazoles incorporated indirectly into salicylamide moiety at position 2 were synthesized. Also the synthesis of novel series of 3-salicylamido-2-hydroxypropyl-amino derivatives were prepared. Several of these compounds were screened for antiinflammatory, analgesic, antipyretic and ulcerogenic activities.

• 약학회지
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• 제57권5호
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• pp.316-322
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• 2013

The new pyridazinone analogs were synthesized for development of candidates to retain anticancer activity. Various 6-substituted pyridazin-3(2H)-ones were prepared from the pyridazinyl chloride 3a~d via endothermic nucleophilic substitution with hydroxide ion as nucleophile for 2~48 h. Pyridazinyl chloride 3a~d could be converted to hydroxypyridazines (or pyridazin-3(2H)ones) using 1~5 equivalents of water (or 1 equivalent of sodium hydroxide) at reflux in DMF. The tautomerism of lactim form to lactam form was also accomplished in pyridazine derivatives. Formation of pyridazinones 10 was undertaken with stirring using sodium hydroxide at reflux in DMF for 2 h. Synthetic compounds were identified using NMR spectrum.

• 약학회지
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• 제49권1호
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• pp.56-59
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• 2005

We synthesized new N-substituted 3-amino-6-chloropyridazine derivatives which were expected to retain biological activity. All synthetic process from pyridazine to 3-aminopyridazines could be carried out conveniently in high yield. N-Substituted 3-amino-6-chloropyridazine derivatives were prepared through amination and acylation from 3,6-dichloropyridazine. 3-Amino-6-chloropyridazine was prepared from the reaction of 3,6-dichloropyridazine with liquid ammonia under autoclave for 6 hrs. The refluxing of 3-amino-6-chloropyridazine and the corresponding acid anhydride for $1{\sim}2$ hrs afforded the N-substituted 3-amino-6-chloropyridazines. Alkyl chain of N-substituent was prolonged to six carbon (hexanoic acid).

• Bulletin of the Korean Chemical Society
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• 제13권1호
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• pp.32-36
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• 1992

The gas-phase pyrolysis reactions of 2-alkoxypyrimidines(II), 2-alkoxypyrazines(III), 4-ethoxypyrimidine(IV) and 3-ethoxypyridazine(V) are investigated theoretically using the AM1 MO method. These compounds pyrolyze in a concerted retro-ene process with a six-membered cyclic transition state (TS). The relative order of reactivity if (IV)>(II)>(III)>(V), which can be rationalized by the two effects arising from electron-withdrawing power of the aza-substituent: (ⅰ) Electron withdrawal from the C-O bond accelerates the rate and (ⅱ) electron withdrawal from the $N^1$-atom, that is participating in the six-membered TS, deactivates the reaction. We are unable to explain the experimental result of the greatest reactivity for pyridazine, (V), with our AM1 results. The reactivity increase accompanied by successive methylation of the ethoxy group, ethoxytert-butoxy, is due to a release of steric crowding in the activation process.

• 약학회지
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• 제13권2_3호
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• pp.51-56
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• 1969

In quantitative analysis of sulfonamide drugs by means of infrared Spectrophotometry, the author tried to analyse Sulfamethoxydiazine and Sulfamethoxypyridazine in their Pharmaceutical Preparations. By the survey of infrared absorption spectra of Sulfamethoxydiazine and Sulfamethoxypyridazine. We found quantitative properties at the peaks of wave number 1150 cm$^{-1}$ (Sulfamethoxydiazine) and 1090 cm$^{-1}$ (Sulfamethoxypyridazine) in the spectra. These peaks obey Beer's Law in a range of 50-150 ug for Sulfamethoxydiazine and 70-350 ${\mu}$g for Sulfamethoxypyridazine in 300 mg KBr disc. By this method, Sulfamethoxydiazine and Sulfamethoxypyridazine could be analyzed less than 2% error.

• Bulletin of the Korean Chemical Society
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• 제11권3호
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• pp.228-231
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• 1990

Some substituted pyridazin-6-ones(1-4) and two uracils(10,12) have been converted to the corresponding $N_1$-(2-oxopropyl)pyridazine-6-ones(6-9), 1,3-bis(2-oxopropyl)-5-fluorouracil(11) and 2-(2-oxopropylthio)uracil(13) respectively by reaction with 4-bromoacetoacetic acid. Also, 4,5-dichloro-1-(3-carbomethoxy-2-oxopropyl)pyrida zin-6-one(15) and 4,5-dichloro-3-nitro-1-(3-carbomethoxy-2-oxopropyl)pyridazin-6-one(16) was synthesized from the corresponding pyridazin-6-ones(1,2) and methyl 4-bromoacetoacetate.

• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2-2
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• pp.172.2-173
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• 2003

3-Alkoxy-6-allylthiopyridazine derivatives showed the strongest protective effect against oxidative stress and their anticancer effect determined on the growth of SK-Hep-l hepatocellular carcinomar cells. The allythio group as a pharmacologically active group was introduced into pyridazine nucleus and a substituent such as halogen or alkoxy was also introduced into paraposition of allylthio group. Five kinds of 3-alkoxy-6-allylthiopyridazine derivatives were synthesized and their chemoprotective activities examined in rats exposed to aflatoxin $B_1$-toxicant. (omitted)

• 대한화학회지
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• 제55권2호
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• pp.230-234
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• 2011

4,5-Dihydro-6-(4-methoxy-3-methylphenyl)-3(2H)-pyridazinone derivative계 화합물의 합성연구를 수행하였다. 첫 번째로, 4,5-dihydro-6-(4-methoxy-3-methylphenyl)-3(2H)-pyridazinone (1)은 o-cresyl methyl ether와 succinic anhydride를 Friedel-Crafts 아실화 반응을 통하여 얻은 다음에, 고리화 반응을 통하여 합성하였다. 얻어진 화합물 1을, NaOEt조건 하에서, 방향족 알데히드와 반응시켜서 4-substituted benzyl pyridazinones (3a-d)을 합성하였으며, 화합물 1을 탈수소화반응을 시켜서 화합물 4를 얻었다. 한편 pyridazine 5는 화합물 1과 1,3-diphenyl-2-propen-1-one을 Michael 첨가반응을 이용하여 합성하였다. N-Dialkylaminomethyl 화합물 6a-b는 pyridazinone 1과 formaldehyde 및 2차 amine을 바능시켜서 얻은 반면에, 화합물 7은 pyridazinone 1을 반응시켜서 얻었으며, 화합물 8은 pyridazinone 3b를 phosphorus oxychloride 와 반응시켜서 얻었다.