• 약학회지
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• 제29권1호
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• pp.39-42
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• 1985

Betaines of bicyclic imidazo-thiazoles were synthesized by the reaction of clectrophiles such as methyl isocyanate, methyl isothiocyanate, allyl isothiocyanate and ketene with 3-methyl and 3-phenyl-5, 6-dihydroimidazo [2,1-b] thiazole. In this reaction, the methyl group which was substituted at 3-position increased the yields of the products in comparison with those from phenyl group substituted substrates. Also, the betaines reacted with methyl iodide to give imidazo-thiazolium salts which were unstable at high temperature and converted the quaternary ammonium salts of original biheterocycles.

• Bulletin of the Korean Chemical Society
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• 제31권10호
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• pp.2854-2860
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• 2010

Synthesis of a new series of pyrimidinyl-imidazo[2,1-b]thiazole derivatives is described. Their antiproliferative activity against A375 human melanoma cell line was tested and the effect of substituents on the pyrimidinyl ring side chain was investigated. The biological results indicated that most of the newly synthesized compounds showed moderate activity against A375, compared with Sorafenib. Among all of these derivatives, the cyclic sulfamide derivatives IIIa, IIIb, and IIIe showed the most potent antiproliferative activity against A375 human melanoma cell line. The IC50 values of compounds IIIa,b were in nanomolar scale. In addition, compound IIIe ($IC_{50}=1.9\;{\mu}M$) also demonstrated more potent antiproliferative activity compared with Sorafenib ($IC_{50}=5.6\;{\mu}M$).

• Bulletin of the Korean Chemical Society
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• 제31권8호
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• pp.2337-2340
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• 2010

A series of new 6-aryl-3-(3,4-dimethoxy-phenyl)-2-phenylsulfanyl-imidazo[2,1-b]-thiazole (5a-c) and 6-aryl-2-benzenesulfonyl-3-(3,4-dimethoxy-phenyl)imidazo[2,1-b]- thiazole (6a-c) have been prepared and characterized by analytical and spectral methods. The title compounds 5a-c and 6a-c were obtained by the reaction of 4-(3,4-dimethoxy-phenyl)-5-phenylsulfanyl-thiazol-2-ylamine (3) and 5-benzenesulfonyl-4-(3,4-dimethoxy -phenyl)thiazol-2-ylamine (4) with various phenacyl bromides in anhydrous ethanol. These newly synthesized compounds (5a-c and 6a-c) were screened for their anthelmintic and anti-inflammatory activities, where they have displayed better activities.

• 약학회지
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• 제35권5호
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• pp.368-371
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• 1991

For the development of new antiulcer agents 5, 6-dihydroimidazo[2, 1-b]- thiazoles substituted at the 3-position are sythesized. Thus, the reaction of 3-chloromethyl-5, 6-dihydroimidazo[2, 1-b]thiazole(2) with thiourea and subsequently with 3-chloro-propionitrile gives 3-[3-[5, 6-dihydroimidazo[2, 1-b]thiazolyl]methylthio]propionitrile(4), which by partial alcoholysis with methanol is converted into methyl-3-[3-[5, 6-dihydro-imidazo[2, 1-b]thiazoyl]methylthio]propionimidate(5) . This compound(5) is treated finally with sulfamide or sulfonamides. 3-[3-[5, 6-dihydroimidazo[2, 1-b]thiazoyl]methylthiol-N$^{2}$-sulfamoyl-propionamidine(6) inhibited gastric acid secretion (45%) when administered intraduodenally (100 mg/kg) to pylorus-ligated rats.

• Bulletin of the Korean Chemical Society
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• 제9권3호
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• pp.164-166
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• 1988

7-Dithiocarboxy-3-phenyl-5,6-dihydro imidazo[2,1-b]thiazolium-betaine (2) was prepared by treatment of 3-phenyl-5,6-dihydro imidazo[2,1-b]thiazole (1) with carbon disulfide in acetone at room temperature. On the reaction of 2 with para-substituted phenacyl bromides (4) having the electron withdrawing property by virtue of (+) resonance (R) < (-) inductive (I) or (-) resonance (R), (-) inductive (I) effect, ring transformation product p-substituted-2-[2-[7-(p-substituted benzoyl)-5-thioxo-2,3-dihydro-1H-imidazo[1,2-c] thiazol-1-yl]-2-phenylvinylthio] acetophenone (6) was obtained; however, when R is electron donating grops with (+) resonance (R) > (-) inductive (I) effect the quarternary ammonium salt 7-(p-substituted phenyl) carbonyl methyl-3-phenyl-5,6-dihydro imidazo [2,1-b] thiazolium bromide (8) is formed. The reaction of 2 with unsubstituted-phenacyl bromide (R = H), on the other hand, gives 6a and 8a to the similar ratio, respectively.

• Archives of Pharmacal Research
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• 제23권2호
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• pp.99-103
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• 2000

Acid and base catalyzed intramolecular cyclizations of N-benzoylthioureidoacetal, contain-ing four functional groups adjacent to thiourea such as benzocarbamoyl, acetal, thioure and amide, were investigated. The condensation reaction of N-benzoyl thiocarbamoylgly-cine amide in the presence of 10% aqueous NaOH provided 1-(2,2-dimethoxy)ethyl-imi- dazolidine-2-thione exclusively. In the presence of pyridine, it was transformed to 2- thiohydantoin. N-Benzoyl thiocarbamoyl glycine amide was completely transformed to an iminothiazolidine exclusively in the presence of Lewis acid such as borontrifluoride ether-ate or trimethylsilyl iodide. 1-(2,2-Dimethoxy)ethyl-imidazolidine-2-thione was transformed to imidazole[2,1-b]thiazole and pyrazino[5,1-a]imidazole in the presence of $BF_3$.$ET_2$O and formic acid, respectively.

• Archives of Pharmacal Research
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• 제13권1호
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• pp.9-13
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• 1990

4, 5-Diphenyl-2-mercaptiomidazole (I) was reacted with hydraziodyl halides IIa-d togive the S-alkyl derivatives III-a-d. Cyclization of IIIa-d afforded imidazo[2, 1-b]-thiazole derivatives Vla, b and VII. Treatment of 1 with a-chloroethylacetoaccetate (IV) gave ethyl 2(4, 5-diphenyl-2-imidazolinylthio)-3-keto-butyrate (V). Compound V coupled with benzendiazonium chloride to give the corresponding phenylhydrazo compound IIId. On heating V with polyphosphoric acid, cyclization took place and 2-acetyl-5, 6-diphenyl-imidazo [2, 1-b] thiazol-3-one (VIII) was obtained. The compound VIII was condensed with aromatic aldehydes to yield the cinnamoyl derivatives 1Xa, b. The antimicrobial activities of compounds IIIa-d, V, VIa, VII were examined.

• 대한수의학회지
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• 제8권1호
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• pp.11-17
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• 1968

가축(家畜)의 선충류에 구충효력이 우수(優秀)하다는 Tetramisole을 이용(使用)하여 폐충인공감염돈에 5, 7, 5, 10, 및 12.5mg/kg을 사료(飼料) 혼여(混與) 및 피하주사(皮下注射)로서 구충효력을 검토(檢討)한 결과(結果) 다음과 같은 성적(成績)을 얻었다. 1. 투약별(投藥別)로 보면 10~12.5mg/kg이 가장 우수(優秀)하였다. 2. 투약별(投藥別)로 보면 사료혼여(飼料混與)가 피하주사법(皮下注射法)보다 우수(優秀)하였고 부작용(副作用)도 적었다. 3. 감염후(感梁後) 4내지 15일(日)째의 유약충에도 구충효과가 있었다. 4. 주요부작용(主要副作用)은 기침, 구토(嘔吐), 흥구(興舊), 호흡수증가등(呼吸數增加等)이었으나 일과성(一過性)으로 곧 소실(消失)되었고 투약(投藥)을 5~12.5mg/kg 범위내(範圍內)에서는 투약량(投藥量)이 따른 부작용(副作用)의 차이(差異)는 인정(認定)되지 않았다.