ChemInform Abstract: New Azole Antifungals. Part 3. Synthesis and Antifungal Activity of 3‐Substituted‐4(3H)‐quinazolinones.

Bartrolí, Javier; Turmo, Enric; Algueró, M.; Boncompte, E.; Vericat, M. L.; Conte, L.; Ramis, Joaquim; García-Rafanell, Julián; Forn, J.

doi:10.1002/chin.199836175

Cited by 24 publications

(29 citation statements)

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“…The study program comprised synthesis of new 3-substituted quinazolin-4-one derivatives via the reactions of the [3,1] benzoxazin-4-one 1 with the nitrogen nucleophiles; hydrazine hydrate, ethyl carbazate, 4-tolylsulfonohydrazide and 2-cyanoacetohydrazide [14], in hot dioxane, to give the quinazolinone derivatives 2-5 ( Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

“…The solid separated was collected by filtration, washed several times with dilute methanol and crystallized from methanol. (13) [1,3] oxazin-4-one (1) was prepared by reaction of dodecanoylchloride with 2-amino-5-bromobenzoic acid, following the most expedition method [13] (Figure 1). The structure of 1 was inferred from its IR spectrum that revealed strong absorption bands at 1757 and 1642 cm-1, attributable to absorption band for C=O and C=N, group respectively.…”

Section: Synthesis Of Compound 13mentioning

confidence: 99%

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Synthesis of Novel 2,3-Disubstituted Quinazolin-4-(3H)-ones and Their Antibacterial Activity on the Ultra-structure of Some Pathogenic Microorganisms

2017

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The fused heterocyclic quinazolin-4-one and related derivatives are of considerable interest due to their wide range of biological properties, for example, anti-tumor[1], antimicrobial [2], antifungal [3] and antibacterial [4]. Moreover, the quinazolin-4-one ring is a frequently encountered unit in natural products, such as L-Vasicinone[5] and chrysogine [6] and in drugs, such as methaqualone [7], isofebrifugine [8] and febrifugine [9]. Aforementioned findings prompted the authors to synthesize a variety of new 2,3-disubstituted quinazolin-4-one derivatives, using the key starting 6-bromo-2-undecylbenzo [3,1] oxazin-4-one [10]. Furthermore, some of the prepared quinazolin-4-one derivatives were used as precursors for synthesis of 1,3-thiazolidin-4-ones and its derivatives which is an important ring for its wide biological applications [11][12][13]. Thus, by merging of these two biologically active hetero-rings together, it was hoped to obtain some new compounds of anticipated pharmaceutical interest. University, Mrorst., 62517, East Beni-Suef, Beni-Suef, Egypt, е-mail: fathykhaled905_7@yahoo.com A SERIES of highly functionalized quinazolin-4-ones, with different substituents at position 3, have been concisely synthesized in good yields, via the reactions of 3-amino-6-bromo-2-undecyl-quinazoline-4(3H)-one with one carbon donor phenyl isothiocyante, followed by α-chlorinated compounds and 1,2-dichloroethanone. Moreover, reactions of 6-bromo-2-undecyl-4H-benzo-[3,1]oxazin-4-one with different hydrazides were also examined, giving new 3-substituted quinazolin-4-one derivatives. Some of the new quinazolin-4-ones were screened against gram negative and positive bacteria and showed good to moderate antibacterial activity. Structures of all new synthesized compounds in this investigation were substantiated using spectroscopic IR, 1 H-NMR and MS studies. Synthesis of Novel

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confidence: 99%

Section: Synthesis Of Compound 13mentioning

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Synthesis of Novel 2,3-Disubstituted Quinazolin-4-(3H)-ones and Their Antibacterial Activity on the Ultra-structure of Some Pathogenic Microorganisms

2017

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“…Some of them have exhibited promising pharmacological activities, such as anticonvulsant, antihypertensive, antidiabetic, antibacterial, antitumor, antihistaminic, and antiinflammatory activities [2][3][4][5][6]. Hence these heterocycles have become an attractive target for combinatorial chemistry groups involved in drug discovery and crop protection.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 3-(3-aminopropyl)-2-(p-tolylamino)quinazolin-4(3H)-one, C18H20N4O

Wang

Xiao

Yang

2013

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialTo a solution of ethyl 2-((triphenylphosphoranylidene)amino)-benzoate iminophosphorane (1.27 g, 3 mmol) in THF (10 mL), 1-isocyanato-4-methylbenzene (0.41 g, 3 mmol ) was added under nitrogen atmosphere at 0-5°C. After the reaction mixture stood for 12 h in 0-5°C to give ethyl 2-(((p-tolylimino)methylene)-amino)benzoate, which was directly used without further purification, whereafter the above resulting solution was added dropwise to propane-1,3-diamine (0.33 g, 4.5 mmol) in THF 5 mL and stirred for 24 h at room temperature. The mixture was concentrated under vacuum until a slightly viscous solution was generated, followed by precipitation in CH 3 OH to give the title compound in 65% yield. Crystals suitable for single-crystal Xray diffraction were obtained by recrystallization from a mixed solvent of methanol and dichloromethane (1:2 = v/v) at room temperature. 1 H NMR (DMSO-d 6 , 500 MHz) d: 7.95 (d, -NH-, J = 7.8 MHz, 1H), 7.60 -7.49 (m, Ar-H, 3H), 7.24-7.13 (m, Ar-H, 5H), 5.43 (s, NH 2 , 2H), 4.17 (t, Quinazolinone-CH 2 -, J 1 = 5.00 Hz, J 2 = 5.95 Hz, 2H), 2.63 (t, -CH 2 -NH 2 , J 1 = 5.95Hz, J 2 = 5.50 Hz, 2H), 2.29 (s, CH 3 , 3H), 1.92 (m, -C-CH 2 -C-, 2H).13 C NMR (DMSO-d 6 , 125 MHz) d: 162.8, 134.6, 132.1, 129.4, 126.7, 123.0, 122.3, 117.7, 37.0, 29.7, 21.0. Experimental detailsThe structure was solved by direct methods with the SHELXS-97 program [1] yielding four crystallographic independant molecules in the asymmetric unit. All H-atoms were positioned with idealized geometry and refined isotropic (U iso (H) = 1.5U eq (C) for methyl H atoms and U iso (H) = 1.2U eq (C) for all other H atoms) using a riding model with C-H = 0.93 Å, 0.97 Å and = 0.96 Å, N-H = 0.86 Å.

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“…It is a very important heterocycle exhibiting excellent pharmacological activities such as antimicrobial [2], antifungal [3], antitumor [4], anticancer [5], antiinflammatory [6], antidepressant [7] and anticonvulsant [8] activities. 3-Aryl-2-thioxo-2,3-dihydroquinazolin-4(1H)-one are a subclass quinazolinones having a wide range of applications including pharmacological and biological activities and important building blocks a variety of…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Crystal Structure of 1-(3-Fluorophenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

Saeed

Flörke

2011

Crystals

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Abstract:The base catalyzed intramolecular nucleophilic cyclization of 1-(2-bromobenzoyl)-3-(2-fluorophenyl)thiourea (1) in the presence of N,N-dimethyl formamide (DMF) afforded the 1-(3-fluorophenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one (2) by an intramolecular nucleophilic substitution S N Ar mechanism. The structure was supported by the spectroscopic data and unambiguously confirmed by the single crystal Xray diffraction data. It crystallizes in the orthorhombic space group P na2 1 with unit cell dimensions a = 22.430(4), b = 8.1478(16), c = 13.522(3) Å, V = 2471.2(9) Å 3 . There are two independent molecules per asymmetric unit that are linked to centrosymmetric ABdimers via intermolecular N-H…S bonds.

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ChemInform Abstract: New Azole Antifungals. Part 3. Synthesis and Antifungal Activity of 3‐Substituted‐4(3H)‐quinazolinones.

Cited by 24 publications

References 1 publication

Synthesis of Novel 2,3-Disubstituted Quinazolin-4-(3H)-ones and Their Antibacterial Activity on the Ultra-structure of Some Pathogenic Microorganisms

Synthesis of Novel 2,3-Disubstituted Quinazolin-4-(3H)-ones and Their Antibacterial Activity on the Ultra-structure of Some Pathogenic Microorganisms

Crystal structure of 3-(3-aminopropyl)-2-(p-tolylamino)quinazolin-4(3H)-one, C18H20N4O

Synthesis and Crystal Structure of 1-(3-Fluorophenyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one

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