Synthesis and evaluation of the biological activities of some 3-{[5-(6-methyl-4-aryl-2-oxo-1,2,3,4-tetrahydropyrimidin-5-yl)-1,3,4-oxadiazol-2-yl]-imino}-1,3-dihydro-2H-indol-2-one derivatives (original) (raw)
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Synthesis and Antimicrobial Activities of New Indolyl -Pyrimidine Derivatives
2011
The purpose of research was to synthesize a series of new indolyl-pyrimidine-5carbonitriles 2-5 from compound 1.The reaction of 2a with ethylcyanoacetate and aromatic aldehydes in presences of excess ammonium acetate gives 6 a-c while condensation with aromatic aldehydes produces chalcones 7a-c via the Claisen condensation .Structure of the synthesized compounds was confirmed by means of their IR, 1 H-NMR spectral data and elemental analysis .The antimicrobial testing of the synthesized compounds were evaluated. Some of the prepared compounds, 2-(1H-indol-3-yl)-4, 6-dioxo-6, 11-dihydro-4H-pyrimido [2, 1-b] quinazoline-3-carbonitrile 3 and 2-hydrazino-4-(1H-indol-3-yl)-6-oxo-1,6dihydropyrimidine-5-carbonitrile 4 showed high antibacterial activity. Melting points of the synthesized compounds were determined by open end capillary tube method in Boetius melting point microscope and are uncorrected. The purity of the compounds was checked using precoated TLC plates (Merck 60 F254) using chloroform: methanol (3:1) solvent system. The structures of the compounds were characterized by Beckman Infrared Spectrophotometer PU9712 using KBr discs. The structures of the compounds were elucidated by 1 H NMR (Proton Nuclear Magnetic Resonance). The molecular weights of compound were determined by SSQ7000 mass spectrometer at 70 eV. 1 H NMR spectra were recorded on JoelEX270MHz spectrometer using TMS as internal standard. All the new compounds gave satisfactory analytical results (within 0.4 of the theoretical values). All the synthesized compounds (1-7) were purified by successive recrystallization. The purity of the synthesized compounds was checked by performing TLC. The structures of the synthesized compounds were determined on the basis of their FTIR and 1 HNMR data. In accordance with the data obtained from antimicrobial activity, most of the synthesized compounds have shown moderate activity against the tested bacteria while compounds 2-(1H-indol-3-yl)-4, 6-dioxo-6, 11-dihydro-4H-pyrimido [2, 1-b]quinazoline-3-carbonitrile (3) and 2-hydrazino-4-(1H-indol-3-yl)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile (4) showed high antibacterial acivity. Only compounds 1,3,4,7a,7 b and 7c are active against C.albicans.
Medicinal Chemistry Research, 2012
A series of derivatives of trans-3-(2,4,6-trimethoxyphenyl)4,5-dihydroisoxazolo-4,5bis[carbonyl-(4 phenyl)thiosemicarbazide (9) and of trans-3-(2,4,6-trimethoxyphenyl)-4,5-dihydro isoxazolo-4,5-bis(aroylcarbohydrazide) (10a-c) were synthesized from trans-3-(2,4,6-trimethoxyphenyl)-4,5-dihydro-4,5-bis(hydrazenocarbonyl)isoxazole (8). The structures of the compounds were elucidated by both elemental and spectral (IR, NMR, and MS) analysis. Compound 9 shows activity against some bacterial species. No antibacterial activities were observed for compounds 10a-c. The antioxidant activity of the new compounds has been screened. Compound 9 showed higher antioxidant activity using the DPPH (1,1-diphenyl-2-picrylhydrazyl) and ABTS (2'-azino-bis(3-ethylbenzoline-6-sulfonic acid) diammonium salt methods.
Journal of Chemistry, 2013
A series of 5-(2-methyl-1H-indol-3-yl)-1,3,4-oxadiazol-2-amine derivatives (3-5) were synthesized. These previously unknown compounds were characterized by spectral studies and elemental analysis. These compounds were evaluated for their antimicrobial and antioxidant activities. Among all the compounds tested 5d exhibited promising antibacterial, antifungal, radical scavenging, and ferric ions (Fe 3+) reducing antioxidant power (FRAP) activities, whereas the compounds 3b, 4c, and 5e exhibited good FRAP and metal chelating activities. In general compounds containing chloro and methyl substituent exhibited better antimicrobial and antioxidant activities.
Journal of American Science, 2010
Aldol condensation reaction between 3-indolaldehyde 1 and 4-methoxyacetophenone 2 afforded chalcone compounds 3. This compound was reacted with some different reagents such as hydrazine hydrate, phenyl hydrazine, thiosemicarbazide, hydroxylamine, ethyl cyanoacetate, urea and thiourea to give pyrazolines 4a, 4b, 5a, 5b, 6, oxazoline 7, Michael adduct 8, pyranone 9, and oxo 14a and thiopyrimidine derivatives 14b, respectively. The structures of all the compounds were confirmed by microanalyses and various spectral data. Some of the synthesized new compounds were screened against antitumor and antimicrobial activity.
2014
A novel series of 2-(5-substituted)-1,3,4-oxadiazole-2-yl)-H-imidazo[1,2,α]pyridine derivatives 5a-i and 6a-d are synthesized and characterized by IR, H NMR, C NMR and Mass spectral analysis. All the synthesized compounds were tested for there antibacterial and antifungal activity of which compound 5b, 5c, 5d, 5e, 5f, 5g, 5h, 5i, 6a, 6c and 6d exhibited good antimicrobial activity.
Arabian Journal of Chemistry, 2016
A series of derivatives of trans-3-(2,4,6-trimethoxyphenyl)4,5-dihydroisoxazolo-4,5bis[carbonyl-(4 phenyl)thiosemicarbazide (9) and of trans-3-(2,4,6-trimethoxyphenyl)-4,5-dihydro isoxazolo-4,5-bis(aroylcarbohydrazide) (10a-c) were synthesized from trans-3-(2,4,6-trimethoxyphenyl)-4,5-dihydro-4,5-bis(hydrazenocarbonyl)isoxazole (8). The structures of the compounds were elucidated by both elemental and spectral (IR, NMR, and MS) analysis. Compound 9 shows activity against some bacterial species. No antibacterial activities were observed for compounds 10a-c. The antioxidant activity of the new compounds has been screened. Compound 9 showed higher antioxidant activity using the DPPH (1,1-diphenyl-2-picrylhydrazyl) and ABTS (2'-azino-bis(3-ethylbenzoline-6-sulfonic acid) diammonium salt methods.
Abstract: Indole, the bicyclic ring system consists of pyrrole ring fused with benzene ring. Although indole moiety is very small but is fascinated by scientists because of the diverse biological activities by not only indole but its various substituted derivatives as well. In the present study some novel indole derivatives like 6-Chloro-3-[(N,N-diethylamino)(oxo)acetyl]-1-benzyl-N-aryl-1H-indole-5-carboxamide derivatives (IC-1 to IC-10) were synthesized according to the scheme. The synthesized novel indole derivatives have been characterized by using elemental analysis, FT-IR, 1HNMR, 13C NMR spectroscopy and further supported by Mass spectroscopy. Purity of all the compounds has been checked on thin layer chromatographic plate and HPLC technique. All the synthesized compounds were evaluated for anti-inflammatory and antipyreticactivities. All the compounds exhibited moderate to significant anti-inflammatory and antipyreticactivities.
Synthesis, and Biological Evaluation of Somw Novel Indolyl - Pyrimidine Derivatives
2015
Article History: A novel series of required intermediate 5-((5-substituted3-phenyl-1H-indol-2-yl) methyleneamino)-6- amino-1,3-dimethylpyrimidine-2,4(1H,3H)-diones (3a-c) was prepared on condensation 5,6-diamino- 1,3-dimethylpyrimidine-2,4(1H,3H)-dione (1) with various 5- substituted 3-phenyl-1H-indole-2- carbaldehyde (2a-c) gave the respective Schiff bases, which on cyclization with thionly chloride afforded targeted compound 8-(5-substituted 3-phenyl-1H- indol-2-yl)-1,3-dimethyl-1H-purine- 2,6(3H,7H)-diones (4a-c). These newly synthesized compounds were screened for their antimicrobial and antioxidant activities, Compounds 3c, 4a and 4c exhibited promising antimicrobial activity. Compounds 3a, 3b, 4a and 4b showed potency of antioxidant activities.
Chemistry Journal of Moldova, 2019
In this study, new pyrazole, imidazole, pyrimidine derivatives having imidazo[4,5-b]indol moiety were successfully synthesized, elucidated by spectroscopic techniques, and evaluated as potential antimicrobial agents. The structure-activity relationship was investigated to obtain a better understanding of the relationship between the chemical structure of the synthesized compounds and their corresponding biological activity. Compounds 2b and 3b exhibited potent antibacterial activities against Bacillus subtilis bacteria comparable to that of Ampicillin standard. Structure-activity relationship studies revealed that the presence of withdrawing carbonyl group on 5-position of pyrazole moiety 2b, phenylpyrazole moiety 3b led to an enhancement in the antibacterial activity of pyrazole derivatives. Furthermore, the presence of carbonyl group on 2-position of the pyrimidine ring of compounds 4a, 5a and 6a has a significant effect on their antibacterial activity against Bacillus subtilis. The antifungal studies indicated that compounds 3b, 4b, 7 and 9 have comparable antifungal activity to that of standard Amphotericin B against Candida albicans and Aspergillus flavus fungi.
Archiv der Pharmazie, 2008
Condensation of aryl hydrazines with ethyl pyruvate gave the respective hydrazones 4 -6; Fischer indolization led to substituted-1H-indole-2-carboxylic acid ethyl esters 7 -9. The Mannich reaction of these compounds with formaldehyde and morpholine yielded ethyl 3-(morpholinomethyl)-substituted-1H-indole-2-carboxylates 10-12. The 5,7-dichloro-1H-indole-2-carbohydrazide 13 was cyclized with methyl orthoformate in DMF to give 6,8-dichloro[1,2,4]triazino[4,5-a]indol-1(2H)-one 14. Vilsmeier -Haack formylation of 7-9 gave ethyl 3-formyl-substituted-1H-indole-2carboxylates 15 -17 whose 2,29-((5-chloro-2-(ethoxycarbonyl)-1H-indol-3-yl)methylene)bis-(sulfanediyl) diacetic acid 18 was prepared. The reaction of 15 and 16 with substituted anilines by conventional and microwave methods gave ethyl 3-(N-aryliminomethyl)-5-halo-1H-indole-2-carboxylates 19 -29. In a cyclocondensation reaction of 19 -25 with thiolactic acid or thioglycolic acid substituted indolylthiazolidinones 30 -33 were prepared. Reaction of hydrazine hydrate with 15 -17 did not give the respective hydrazones but directly led to the cyclized products substituted-3H-pyridazino[4,5-b]indol-4(5H)-ones 34 -36, while a reaction with 2,4-dichlorophenylhydrazine yielded the uncyclized hydrazones. The chlorination of 35 and 36 with POCl 3 gave pyridazino[4,5-b]indoles 39 and 40, respectively; reaction of the latter compounds with morpholine gave 4-(substituted-5H-pyridazino[4,5-b]indol-4-yl)morpholine 41 and 42. Mannich reaction of 34 with formaldehyde and N-ethylpiperazine gave 8-chloro-3-((4-ethylpiperazin-1-yl)methyl)-3H-pyridazino [4,5-b]indol-4(5H)-one 43. The microwave assistance of selected reactions has a profound effect on the reaction speed. The structures of the new compounds were confirmed by both analytical and spectral data. Some compounds were subjected to investigations concerning their antimicrobial, tranquilizing, and anticonvulsant activities.