Cyclization of lactamimide ketones to imidazo[1,2-.alpha.]azacycloalkanes with hypoglycemic activity

Gp, Claxton; Jm, Grisar; Nl, Wiech

doi:10.1021/jm00249a027

Cited by 13 publications

(7 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…3-Aryl-6,7-dihydro-5 H -pyrrolo[1,2- a ]imidazoles 3a – e and 3-aryl-6,7,8,9-tetrahydro-5 H -imidazo[1,2- a ]azepines 8a – d were obtained through the condensation of 5-methoxy-3,4-dihydro-2 H -pyrrole 1 or 7-methoxy-3,4,5,6-tetrahydro-2 H -azepine 7 with 2-amino-1-arylethanone 2a – e using a well-known technique [ 19 ]. 2-Bromo-1-(2-difluoromethoxyphenyl)-ethanone (reagent for synthesis of 10a ) was synthesized using a known method [ 20 ].…”

Section: Resultsmentioning

confidence: 99%

“…3-Phenyl-1-[2-(4-methylphenyl)-2-oxoethyl]-6,7,8,9-tetrahydro-5 H -imidazo[1,2- a ]azepin-1-ium bromide ( 10g ) was obtained using the method of [ 19 ].…”

Section: Methodsmentioning

confidence: 99%

“…1-Substituted-3-aryl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-1-ium chlorides 4, 5, 6ae and 1-substituted-3-aryl-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-1-ium chlorides or bromides 8, 9, 10a-h, 11, 12 were synthesized by Schemes 1 and 2. 3-Aryl-6,7-dihydro-5H-pyrrolo [1,2-a]imidazoles 3a-e and 3-aryl-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepines 8a-d were obtained through the condensation of 5-methoxy-3,4-dihydro-2H-pyrrole 1 or 7-methoxy-3,4,5,6-tetrahydro-2H-azepine 7 with 2-amino-1arylethanone 2a-e using a well-known technique [19]. 2-Bromo-1-(2-difluoromethoxyphenyl)-ethanone (reagent for synthesis of 10a) was synthesized using a known method [20].…”

Section: Chemistrymentioning

confidence: 99%

See 2 more Smart Citations

Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5H-pyrrolo[1,2-a]imidazole and 5H-Imidazo[1,2-a]azepine Quaternary Salts

et al. 2021

View full text Add to dashboard Cite

A series of novel 3-aryl-5H-pyrrolo[1,2-a]imidazole and 5H-imidazo[1,2-a]azepine quaternary salts were synthesized in 58–85% yields via the reaction of 3-aryl-6, 7-dihydro-5H-pyrrolo[1,2-a]imidazoles or 3-aryl-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepines and various alkylating reagents. All compounds were characterized by 1H NMR, 13C NMR, and LC-MS. The conducted screening studies of the in vitro antimicrobial activity of the new quaternary salts derivatives established that 15 of the 18 newly synthesized compounds show antibacterial and antifungal activity. Synthesized 3-(3,4-dichlorohenyl)-1-[(4-phenoxyphenylcarbamoyl)-methyl]-6,7-dihydro-5H-pyrrolo[1,2-a]imidazol-1-ium chloride 6c possessed a broad activity spectrum towards Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, and Cryptococcus neoformans, with a high hemolytic activity against human red blood cells and cytotoxicity against HEK-293. However, compound 6c is characterized by a low in vivo toxicity in mice (LD50 > 2000 mg/kg).

show abstract

Section: Resultsmentioning

confidence: 99%

“…3-Phenyl-1-[2-(4-methylphenyl)-2-oxoethyl]-6,7,8,9-tetrahydro-5 H -imidazo[1,2- a ]azepin-1-ium bromide ( 10g ) was obtained using the method of [ 19 ].…”

Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5H-pyrrolo[1,2-a]imidazole and 5H-Imidazo[1,2-a]azepine Quaternary Salts

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Chlorohydrate a-amino-4-chloroacetophenone 2 was obtained [13] by condensation of a-bromo-4chloroacetophenone with hexamethylenetetramine. 3-(4-Chlorophenyl)-6,7,8,9-tet rahydro-5Н-imidazo[1,2-a]azepine 3 was obtained by methods [14,15].…”

Section: кEy Words: Anticancer Activity 5-fluorouracil Derivatives mentioning

confidence: 99%

Synthesis and anticancer activity of 1-(41-isopropylphenyl)-4-(42-chlorophenyl)5,6,7,8-tetrahydro-2,4a-diazacyclopenta[ cd ]azulene-2-carboxylic acid arylamides against PC-3 prostate cancer cells

Demchenko

Fedchenkova

Bukhtiarova

et al. 2019

Фармакологія та лікарська токсикологія

View full text Add to dashboard Cite

Pharmacotherapy of prostate cancer is an important part in combating oncologic diseases. This is very relevant, because prostate cancer is a cause of 10 % of deaths from all cancerous diseases in males. The aim of the study – to synthesize novel derivatives of 1-(41-isopropylphenyl)-4-(42-chlorophenyl)5,6,7,8-tetrahydro-2,4а-diazacyclopenta[cd]azulene-2-carboxylic acid arylamides and to evaluate their antitumor activity against PC-3 prostate cancer cells. By reaction of equimolar amounts of 2-methoxy-3,4,5,6-tetrahydro-7H-azepine with a-amino-4-chloroacetophenone chlorohydrate, 3-(4-chlorophenyl)-6,7,8,9- tetrahydro-5Н-imidazo[1,2-a]azepine was synthesized. By alkylation of a-bromo-4-іsopropylacetophenone in ethylacetate and following treatment of the obtained intermediary quaternary salt with excess of 5 % NaOH solution,1-(41-isopropylphenyl)-4-(42chlorophenyl)-5,6,7,8-tetrahydro-2,4а-diazacyclopenta[cd] azulene was synthesized. By boiling it with equimolar amounts of correspondding arylisocyanates in dried benzol, an array of 1-(41-iso propylphenyl)-4(42-chlorophenyl)-5,6,7,8-tetrahydro-2,4а-diazacyclopenta[cd]azulene-2-carboxylic acid arylamides were synthesized. Structure and purity of all compounds obtained were confirmed by data of MR1Н spectroscopy. Lipophilicity (LogP) of compounds 6 and 8 a-i was calculated with the ACD LogP program. Antitumor activity of 1-(41-isopropylphenyl)-4-(42-chlorophenyl)-5,6,7,8-tetrahydro-2,4а-diazacyclopenta[cd]azulene-2-carboxylic acid (3-methylphenyl) and (3-methoxyphenyl)-amides was evaluated at in vitro test on prostate cancer PC-3 cell lines. It is indicated, that at concentration of 10–5 M these compounds exceed 5-fluorouracil as comparison drug in inhibiting PC-3 prostate cancer cells growth by 52.32 % and 3.93 % correspondingly. The data obtained substantiate feasibility of further studies of 1-(41-isopro pylphenyl)-4-(42-chlorophenyl)-5,6,7,8-tetrahydro-2,4а-diazacyclopenta[cd] azulene-2-carboxylic acid arylamides as new, potential antitumor medicines for prostate cancer treatment.

show abstract

“…Reports of synthesis of annelated imidazoles and benzimidazoles include methods that are limited to the preparation of either annelated imidazoles [2][3][4] or annelated benzimidazoles. [5][6][7][8] Despite the structural similarities of imidazole and benzimidazole, there are no reports of methods for the synthesis of these fused ring derivatives that have the potential for application to both the imidazole and benzimidazole ring systems.…”

Section: Figurementioning

confidence: 99%

Synthesis of Annelated Imidazoles and Benzimidazoles

2000

Synlett

View full text Add to dashboard Cite

A variety of fused ring imidazole or benzimidazole derivatives were prepared through two successive condensations of a dihalide with 4,5-diphenylimidazole or benzimidazole. The 2-methyl substituted derivatives of 4,5-diphenylimidazole or benzimidazole were also used. The size of the annelated ring, which is dependent on the dihalide used, can be varied from five to seven atoms. Initially, N-alkylhalo derivatives were prepared by condensation of the heterocyclic starting materials with a dihalide. Ring closure was then effected through intramolecular condensation of a carbanion derived from the 2-position or the 2-methyl group of the parent heterocyclic ring with the N-alkylhalo moiety.

show abstract

Cyclization of lactamimide ketones to imidazo[1,2-.alpha.]azacycloalkanes with hypoglycemic activity

Cited by 13 publications

References 1 publication

Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5H-pyrrolo[1,2-a]imidazole and 5H-Imidazo[1,2-a]azepine Quaternary Salts

Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5H-pyrrolo[1,2-a]imidazole and 5H-Imidazo[1,2-a]azepine Quaternary Salts

Synthesis and anticancer activity of 1-(41-isopropylphenyl)-4-(42-chlorophenyl)5,6,7,8-tetrahydro-2,4a-diazacyclopenta[ cd ]azulene-2-carboxylic acid arylamides against PC-3 prostate cancer cells

Synthesis of Annelated Imidazoles and Benzimidazoles

Contact Info

Product

Resources

About