Synthesis and in vitro antitumor activities of novel 4-anilinoquinazoline derivatives

Chandregowda, Venkateshappa; Kush, Anil; Reddy, G. Chandrasekara

doi:10.1016/j.ejmech.2008.07.023

Cited by 121 publications

(79 citation statements)

References 15 publications

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“…Thus, the reaction of 2 with AC 2 O afforded 1-(9-arylidene-3-methyl-5-aryl-6,7,8,9-tetrahydro [1,2,4]triazolo [3,4-b]quinazolin-1(5H)-yl)ethanone 3 on acetylation followed by cyclization 23 . The structure of compound 3 was characterized by FT-IR spectrum which showed the disappearance of the characteristic bands for NHNH 2 groups and appearance of absorption band at 1736 cm -1 corresponding to carbonyl acetyl group.…”

Section: Resultsmentioning

confidence: 99%

“…The 1 H NMR spectrum revealed two singlets of six protons at δ 1.2, 2.5 ppm for 2CH 3 groups. Condensation of compound 3 with thiosemiarbazide yielded the corresponding 1-(1-(9-arylidene-3-methyl-5-phenyl-6,7,8,9-tetrahydro- [1,2,4] triazolo [3,4-b]quinazolin-1(5H)-yl)ethylidene)thiosemicarb-azide 4. FT-IR spectrum showed absorption bands at 3421, 3235, 3125 and 1274 cm -1 attributable to NHNH 2 and C=S groups, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…The solid was filtered and recrystallized from methanol to give compound 4. Synthesis of 1-(1-(9-arylidene-3-methyl-5-phenyl-6,7,8,9-tetrahydro- [1,2,4]triazolo- [3,4-b] quinazolin-1(5H)-yl)ethylidene)thiosemicarbazide Schiff's base (5) To ethanolic solution of compound 4 (0.01 mol), 2-chlorobenzaldehyde (0.01 mol) was added. Synthesisof1- (9-arylidene-3-methyl-5-phenyl-6,7,8,9-tetrahydro-[1,2,4]triazolo [3,4-b] 5-phenyl-6,7,8,9-tetrahydro-[1,2,4]triazolo [3,4-…”

Section: Quinazolin-1(5h)-yl)ethylidene)thiosemicarbazide (4)mentioning

confidence: 99%

“…The solid separated was collected, filtered and recrystallized from ethanol to give compound 11. 1,4,5,7,8,9,10,11-octahydro- [1,2,4 ]triazepino [3,4-b]quinazoline-4-carbonitrile (12) To ethanolic solution of compound 2 (0.1 mol) containing (5 mL) piperidine, 2-chlorobenzaldehde (0.01 mol) and malononitrile (0.01 mol) were added. The reaction mixture was heated under reflux for 8 h, cooled to room-temp, poured onto crushed ice containing conc.…”

Section: Synthesis Of 9-arylidene-5-phenyl-126789-hexahydro-[12mentioning

confidence: 99%

“…Quinazoline derivatives, which belong to the N-containing heterocyclic compounds, have caused universal concerns due to their biopharmaceutical activities. Researchers have already determined many therapeutic activities of quinazoline derivatives, including anticancer [1][2][3][4] , antiinflammatory 5,6 , antibacterial [7][8][9][10] , analgesic 5,9 , antiviral 11 , anticytotoxic 12 , antispasm 9,13 , antituberculosis 14 , antioxidant 15 , antimalarial 16 , antihypertension 17 , antiobesity 18 , antipsychotic 19 , anti-diabetics 20 , etc. Medicinal chemists synthesized quinazoline derivatives with different biological activities by installing various active groups to the quinazoline moiety.…”

Section: Introductionmentioning

confidence: 99%

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Utility of 4-Aryl-8-arylidene-3, 4, 5, 6, 7, 8-hexa-hydroquinazoline-2-thiol for the Synthesis of Some New Heterocycles as Antioxidant Agents

2017

Chem Sci Trans

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Abstract:The present study deals with the synthesis and reactions of 4-aryl-8-arylidene-3,4,5,6,7,8-hexahydroquinazoline-2-thiol (1). Hydrazinolysis of compound 1 yielded hexahydroquinazolinyl hydrazine 2. Acetylation of compound 2 yielded [1,2,4] triazolo [3,4-b] quinazoline derivative 3. The reaction of compound 2 with diethyl oxalate and ethyl acetoacetate afforded hexahydro quinazolin-2-yl-hydrazinyl-2-oxoacetate 9 and hexahydroquinazolin-2-yl-3-oxobutane hydrazide 10. Treatment of compound 1 with chloroacetyl chloride gave tetrahydro-2H-thiazolo [2,3-b] quinazolin-3(5H)-one 13 which was used as a key for the synthesis of a series of heterocyclic compounds (14-19). The structures of the newly synthesized compounds were elucidated on the basis of elemental analysis, spectral data. The antioxidant activities of some new synthesized compounds have been screened. Compounds 2, 3, 12, 13, 15, 16 and 19 showed antioxidant activity using the DPPH method.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Quinazolin-1(5h)-yl)ethylidene)thiosemicarbazide (4)mentioning

confidence: 99%

Section: Synthesis Of 9-arylidene-5-phenyl-126789-hexahydro-[12mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Utility of 4-Aryl-8-arylidene-3, 4, 5, 6, 7, 8-hexa-hydroquinazoline-2-thiol for the Synthesis of Some New Heterocycles as Antioxidant Agents

2017

Chem Sci Trans

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N‐Arylhydroxylamines and Chemical Carcinogenicity

Novák¹,

Chakraborty²

2010

Patai's Chemistry of Functional Groups

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Two related classes of carcinogens, arylamines (AAs) and heterocyclic arylamines (HAAs), have played an important role in the development of our understanding of chemical carcinogenesis. AAs are largely industrial products or by‐products, but significant exposure also occurs through inhalation of cigarette smoke. HAAs are produced during broiling or frying of meats and fish and are viewed as significant cancer risks in most human populations. AAs and HAAs are properly characterized as procarcinogens because they require metabolic activation into their ultimate carcinogenic forms. Both classes are activated predominately by cytochrome P450 (CYP450) mediated oxidation into N ‐arylhydroxylamines that are further metabolized into acetic or sulfuric acid esters of the hydroxylamines by the action of N ‐acetyltransferases (NATs) or sulfotransferases (SULTs). These esters appear to be the ultimate carcinogens in most cases. Research on the metabolism of AAs and HAAs, the structures of DNA adducts derived from their carcinogenic metabolites, and the relationship of DNA adduct conformations and persistence to observed mutations are reviewed. Evidence for the proposal that the reactive intermediate responsible for the formation of DNA adducts is a nitrenium ion derived from the hydroxylamine esters is the main topic of this review. Future prospects for research in this area are considered. Introduction Metabolic Activation of AAs and HAAs The Structures of DNA Adducts The Nitrenium Ion Hypothesis The Hypothesis Tested Concluding Remarks

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Tumorspezifische, Hypoxie‐basierte Aktivierung von EGFR‐Inhibitoren

et al. 2014

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Die Entwicklung von Rezeptor-Tyrosinkinase-Inhibitoren (TKIs) ist ein Meilenstein in der Entwicklung neuer Tumortherapeutika. Allerdings geht die TKI-Therapie mit starken Nebenwirkungen und Chemotherapieresistenz einher. Ziel dieser Studie war die Synthese und präklinische Entwicklung eines neuen Inhibitors des Epidermalen Wachstumsfaktorrezeptors (EGFR), der durch die spezifischen Eigenschaften des malignen Gewebes aktiviert wird. Zu diesem Zweck wurde ein Co III -basiertes "Prodrug-Design" verwendet, das die gezielte Freisetzung des aktiven EGFR-Inhibitors durch den im soliden Tumor auftretenden Sauerstoffmangel (Hypoxie) ermçglicht. Hierfür wurden mehrere neue EGFRhemmende Liganden mit Chelateinheiten synthetisiert, und derjenige mit dem grçßten EGFR-hemmenden Potenzial wurde für die Komplexierung mit Co III ausgewählt. Anschließend wurden hypoxische Aktivierung und Hemmung des EGFR-Signalwegs nachgewiesen, und eine vielversprechende Aktivität des neuen Komplexes in vivo wurde gezeigt.

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Synthesis and in vitro antitumor activities of novel 4-anilinoquinazoline derivatives

Cited by 121 publications

References 15 publications

Utility of 4-Aryl-8-arylidene-3, 4, 5, 6, 7, 8-hexa-hydroquinazoline-2-thiol for the Synthesis of Some New Heterocycles as Antioxidant Agents

Utility of 4-Aryl-8-arylidene-3, 4, 5, 6, 7, 8-hexa-hydroquinazoline-2-thiol for the Synthesis of Some New Heterocycles as Antioxidant Agents

N‐Arylhydroxylamines and Chemical Carcinogenicity

Tumorspezifische, Hypoxie‐basierte Aktivierung von EGFR‐Inhibitoren

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