Synthesis, X‐Ray Structure, and Pharmacological Activity of Some 6,6‐Disubstituted Chromeno[4,3‐b]‐ and Chromeno[3,4‐c]‐quinolines.

Hegab, Mohamed I.; Abdel-Fattah, Abdel-Samee M.; Yousef, Nabil M.; Nour, Hany F.; Mostafa, Ahmed; Ellithey, Mohey

doi:10.1002/chin.200748140

Cited by 3 publications

(3 citation statements)

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“…The results obtained from the spectra were consistent with the assigned structures of the compounds. The 1 HNMR and 13 CNMR spectra as well as the reaction schemes for the synthesis of the above compounds are outline in the Figs (6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22) The synthesized compounds were subjected to molecular docking with a target protein, 1CVU to compare their binding energies with celecoxib and rofecoxib which are used as standard drugs for the inhibition of COX2 enzyme, Kurumbail (1994). From the docking result, the binding energy values of the above synthesized compounds were found to be -5.8 kJmol -1 , -6.2 kJmol -1 , -7.2 kJmol -1 , -7.4 kJmol -1 and -7.6 kJmol -1 respectively as shown in table 1 and the chart in Fig 23 below.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Preliminary Molecular Docking Studies of Novel Ethyl-Glycinate Amide Derivatives

Eugene

Afoke

Aronimo

et al. 2020

Int. J. Res. Granthaalayah

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Ethyl glycinate was synthesized by the Fischer esterification protocol, and its amide derivatives; 2-amino-N-(nitrophenyl)acetamide 31, 2-amino-N-(6-methylpyridin-2-yl) acetamide 33, N,N'-(1,4-phenylene)bis-(2-aminoacetamide) 35, N,N'-(6-chloropyrimidine-2,4-diyl)bis-(2-aminoacetamide) 37, and 2,4-(diamino-N’N-6-hydroxypyrimidyl)acetamide 39 respectively were obtained by coupling reactions of 4-nitroaniline, 2-amino-6-methylpyridine, 1,4-diamino-N,N’-benzene, 2,6-diamino-4-chloropyrimidine and 2,4-diamino-6-hydroxypyrimidine respectively with ethyl glycinate. These compounds were characterized on the basis of their melting points, UV-Visible, IR, 1HNMR and 13CNMR spectroscopic analyses. The results obtained from the spectra were consistence with the assigned structures of the compounds. The synthesized compounds were subjected to molecular docking with a target protein, 1CVU to compare their binding energies with celecoxib and rofecoxib which are standard drugs that inhibit COX2 enzyme. From the docking results, the binding energies values of the above synthesized compounds are -5.8 kJmol-1, -6.2 kJmol-1, -7.2 kJmol-1, -7.4 kJmol-1 and -7.6 kJmol-1 respectively. Compound 39 showed the highest binding energy of -7.6 kJmol-1, close to celecoxib and rofecoxib with binding energy values of -8.0 kJmol-1 and -8.2 kJmol-1 respectively. This result indicates that compound 39 possess some level of inhibitory activity against COX2.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Preliminary Molecular Docking Studies of Novel Ethyl-Glycinate Amide Derivatives

Eugene

Afoke

Aronimo

et al. 2020

Int. J. Res. Granthaalayah

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“…2,3-Dihydro-2,2-dimethylchromen-4-one (1a) (12), 2,3-dihydro spirochromen(2,1') cyclohexane-4-one (1b) (13), 2,3-dihydro-2-ethyl-2-methylchromen-4-one (1c) (12), 4--chloro-2,2-dimethyl-2H-chromene (2a) (14), 4-chloro spiro-2H-chromene(2,1')cyclohexane (2b) (15), 4-chloro-2-ehyl-2-methyl-2H-chromene (2c) (16), 4-chloro-2,2-dimethyl-2H--chromene-3-carbaldehyde (3a) (6), 4-chloro spiro-2H-chromene(2,1')cyclohexane-3-carbaldehyde (3b) (6), and 4-chloro-2-ethyl-2-methyl-2H-chromene-3-carbaldehyde (3c) (16) were prepared according to the literature.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and pharmacological activities of some condensed 4-chloro-2,2-dialkyl chromene-3-carbaldehyde derivatives

Hegab¹,

Yousef²,

Nour³

et al. 2008

Acta Pharmaceutica

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The Vilsmeier-Haack reaction of active methylene compounds led to the formation of b-halo carbaldehydes, which constitute a class of compounds that served as useful intermediates towards construction of different heterocyclic compounds (1). Accordingly, some of b-chlorocarbaldehydes were described to react with phenylhydrazine and 2-mercapto acetic acid and its ethyl ester to give the corresponding pyrazolo and thieno derivatives (2-6). Pawar and Rajput (7) reported the synthesis of 5-anilinothiazolo- [5,4-d]isoxazole from 4-chloro-2-anilinothiazol-5-carbaldehyde with hydroxylamine hydrochloride. As it is known, oxime ethers have found many uses in recent years as nonsteroidal anti-inflammatory drugs (8), insect growth regulators (9), materials with steroidal effect (10), and as antimicrobial agents (11).In continuation of our study on hindered b-chlorocarbaldehydes (6), it seemed to be interesting to react some hindered b-chlorocarbaldehydes with some hydrazines, thiosemicarbazide, and hydroxylamine hydrochloride and to evaluate the pharmacological activity of the new products as anti-inflammatory and anti-ulcerogenic agents. Some new hydrazono 5a,b, thiosemicarbazono 6a-c, and oximo chromenes 7a-c were prepared via the reaction of the corresponding b-chlorocarbaldehyde 3 with hydrazine, aromatic hydrazine, thiosemicarbazide and hydroxylamine hydrochloride, respectively. In addition, ether derivatives 8a-h were prepared from the corresponding aldoximes 7a-c. The new products were tested for anti--inflammatory and ulcerogenic score activities compared to indomethacin.

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“…A combination of benzopyran or chromen with a quinoline moiety in a single molecule, for example, 6H-chromeno[4,3-b]quinoline (Vu et al, 2007;Hegab et al, 2007 ) or 1-benzopyrano[3,4 -f]quinoline (Tabakovic et al, 1983) have also been identified for the promising bioactive molecules.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of 6H-1-benzopyrano[4,3-b]quinolin-6-one derivatives as inhibitors of colon cancer cell growth

Guo

et al. 2015

Bangladesh J Pharmacol

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A convenient synthesis of 6H-1-benzopyrano [4,3-b]quinolin-6-one derivatives was reported using 4-chloro-2-oxo-2H-chromene-3-carbaldehyde with different aromatic amines using silica sulfuric acid. The compounds were tested for their anticancer activity against colon (HCT-116 and S1-MI-80), prostate (PC3 and DU-145), breast (MCF-7 and MDAMB-231) cancer cells. These compounds showed more selectivity and potent cytotoxic activity against colon cancer cells. 3c was tested against five other colon cancer cell lines (HT-29, HCT-15, LS-180, LS-174, and LoVo), which had similar cytotoxicity and selectivity. 3c did not induce PXR-regulated ABCB1 or ABCG2 transporters. In fact, 3c induced cytotoxicity in HEK293 cells over expressing ABCB1 or ABCG2 to the same extent as in normal HEK293 cells. It was cytotoxic approximately 3-and 5-fold to resistant colon carcinoma S1-MI-80 cells. 3c also produced concentration-dependent changes in HCT-116 colon cancer cells, in mitochondrial membrane potential, leading to apoptosis, and submicromolar concentrations caused chromosomal DNA fragmentation. Article Info

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Synthesis, X‐Ray Structure, and Pharmacological Activity of Some 6,6‐Disubstituted Chromeno[4,3‐b]‐ and Chromeno[3,4‐c]‐quinolines.

Cited by 3 publications

References 1 publication

Synthesis and Preliminary Molecular Docking Studies of Novel Ethyl-Glycinate Amide Derivatives

Synthesis and Preliminary Molecular Docking Studies of Novel Ethyl-Glycinate Amide Derivatives

Synthesis and pharmacological activities of some condensed 4-chloro-2,2-dialkyl chromene-3-carbaldehyde derivatives

Synthesis and biological evaluation of 6H-1-benzopyrano[4,3-b]quinolin-6-one derivatives as inhibitors of colon cancer cell growth

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