The derivatives of the 2a,4a-Diazacyclopenta[c,d]azulene

Ковтуненко, В. А.; Nazarenko, K. G.; Demchenko, A. M.

doi:10.1016/0040-4020(96)00515-7

Cited by 8 publications

(6 citation statements)

References 2 publications

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“…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

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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.

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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

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“…Consequently, the lactim ethers 167 react in the tautomeric form 187a under the investigated conditions [185]. 3-Aryl-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepines 189 were synthesized with yields of 54-74% by condensation of caprolactim methyl ether with the hydrochlorides 190 at room temperature followed by treatment of the reaction mixtures with dilute hydrochloric acid and then with aqueous ammonia to pH 10 [187]. …”

Section: Reactions With Bifunctional Compounds Involving Cyclizationmentioning

confidence: 99%

Five-, Six-, and Seven-membered Lactim Ethers. Methods of Synthesis and Chemical Properties. (Review)

Shvekhgeimer

2005

Chem Heterocycl Compd

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“…(3 H, s, OCH3), 2.95 (2 H, t, 8-CH2), 2.17 (2 H, br.s, 6-CH2), 2.0 ppm (2 H, s, 7-CH2). for C25H23CIN202,%: C 71.68,H 5.53,C1 8.46,N 6.69. 2-Acetyl-l-(4'-bromophenyl)-4-(4" -ani~l)-5, 6,7,d]azulene (II]t) was obtained in 92% yield from base liIb analogously to IIIe. Found, %: C 60.21, H 4.88, N 6.07.…”

Section: ~-(4'-ani~y~)-4-(4"-chl~r~he~y~)~5~6~7~8-tetrahydr~-2a~4a-dimentioning

confidence: 99%

“…N-Methylamide of 1-(4'-ant~l)-4-(4" -chlorophenyl)-5, 6,7,d]azulene-2-carboxylic Acid (IIIi). Methyl isocyanate (0.1 cm 3, 1.6 retool) was added to a solution of base IRa (0.38 g, 1 retool) in benzene (10 cm3).…”

Section: -( 4 '~Brom~phe~y~)-4-( 4 "-Ani~y~)-5~6~ 7 ~8-tetrahydr~-2amentioning

confidence: 99%

“…It therefore was of interest to prepare and investigate functional derivatives of 5, 6,7,8-tetrahydro-2a,4a-diazacyclopenta[c,d] 5,6,7,d]azulenes (IIIa-d) were unchanged on heating with 2 M sodium hydroxide solution or with 2M hydrochloric acid. Analysis showed that azulene can de described as a 10 ,r-electron heteroaromatic system in which the greatest p-electron density is localized on the carbon atoms of the pyrrole part of the tricycle and electrophilic attack should occur exclusively at the free position 2 of the system.…”

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confidence: 99%

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Electrophilic substitution in a series of derivatives of 5,6,7,8-tetrahydro-2a,4a-diazacyclopenta[c,d]azulene

Ковтуненко¹,

Nazarenko²,

Demchenko³

1997

Chem Heterocycl Compd

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The derivatives of the 2a,4a-Diazacyclopenta[c,d]azulene

Cited by 8 publications

References 2 publications

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 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

Five-, Six-, and Seven-membered Lactim Ethers. Methods of Synthesis and Chemical Properties. (Review)

Electrophilic substitution in a series of derivatives of 5,6,7,8-tetrahydro-2a,4a-diazacyclopenta[c,d]azulene

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