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1.
Synthesis of New Triazole and Oxadiazole Derivatives of Quinazolin‐4(3H)‐one and Their Antimicrobial Activity
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Kotla Veena Vani Garlapati Ramesh Chunduri Venkata Rao 《Journal of heterocyclic chemistry》2016,53(3):719-726
A series of new triazole derivatives of quinazolin‐4(3H)‐one and new oxadiazole derivatives of quinazolin‐4(3H)‐one were synthesized. The newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR and mass spectral data. All the newly synthesized compounds were screened for antibacterial activity against Staphylococcus aureus, Bacillus subtilis (gram‐positive bacteria), Escherichia coli, Pseudomonas aeruginosa (gram‐negative bacteria), and antifungal activity was carried out against Candida albicans and Aspergillus niger. 相似文献
2.
Synthesis and Pharmacological Evaluation of 3‐propyl‐2‐substitutedamino‐3H‐quinazolin‐4‐ones as Analgesic and Anti‐Inflammatory Agents
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R. V. Sheorey A. Thangathiruppathy V. Alagarsamy 《Journal of heterocyclic chemistry》2016,53(5):1371-1377
A variety of novel 3‐propyl‐2‐substitutedamino‐quinazolin‐4(3H)‐ones were synthesized by reacting the amino group of 2‐hydrazino‐3‐propyl quinazolin‐4(3H)‐one with a variety of aldehydes and ketones. The starting material 2‐hydrazino‐3‐propyl quinazolin‐4(3H)‐one was synthesized from propylamine. The title compounds were investigated for analgesic and anti‐inflammatory activities. The compound 2‐(1‐ethylpropylidene‐hydrazino)‐3‐propyl‐quinazolin‐4(3H)‐one ( SR2 ) emerged as the most active compound of the series, and it is more potent in its analgesic and anti‐inflammatory activities when compared with the reference standard diclofenac sodium. 相似文献
3.
Design and Synthesis of Novel 3‐(Phenyl)‐2‐(3‐substituted propylthio) Quinazolin‐4‐(3H)‐ones as a New Class of H1‐Antihistaminic Agents
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A series of novel 3‐(phenyl)‐2‐(3‐substituted propylthio) quinazolin‐4‐(3H)‐ones were synthesized by the reaction of 2‐(3‐bromopropylthio)‐3‐(phenyl) quinazolin‐4‐(3H)‐one with various amines. The starting material, 2‐(3‐bromopropylthio)‐3‐(phenyl) quinazolin‐4‐(3H)‐one was synthesized from aniline. When tested for their in vivo H1‐antihistaminic activity on conscious guinea pigs, all the test compounds protected the animals from histamine‐induced bronchospasm significantly. Compound 2‐(3‐(4‐methylpiperazin‐1‐yl) propylthiothio)‐3‐(phenyl) quinazolin‐4(3H)‐one ( Ph5 ) emerged as the most active compound (73.23% protection) of the series when compared with the reference standard chlorpheniramine maleate (70.09% protection). Compound Ph5 shows negligible sedation (5.01 %) compared with chlorpheniramine maleate (29.58%). Therefore, compound Ph5 can serve as the leading molecule for further development into a new class of H1‐antihistaminic agents. 相似文献
4.
Some new derivatives 7‐chloro‐2‐[2‐(2,6‐dichlorophenyl)amino]benzyl‐3‐[4‐(2‐substituted phenyl‐4‐oxo‐ thiazolidin‐3‐yl)phenyl]sulfonamido‐quinazolin‐4(3H)‐ones 5a – 5l were synthesized from 2‐[2‐(2,6‐dichloro‐phenyl)amino]phenyl acetic acid via acid chloride, benzoxazinone, amino quinazolin‐4(3H)‐one and Schiff base formation. The synthesized compounds were screened for in vitro antibacterial and antifungal activities by broth micro dilution method. Some of the Schiff base as well as 4‐thiazolidinone derivatives showed promising antibacterial activity while pronounced antifungal activity was observed against C. albicans. 相似文献
5.
《Journal of heterocyclic chemistry》2018,55(8):1955-1959
Some novel phosphines, aminophosphines and their oxides, and derived phosphorus acids bearing 4‐oxo ‐ 2‐phenylquinazolin‐3‐yl moiety were synthesized. The methodology depended on the reaction of each 2‐phenylquinazolin‐4(3H)‐one ( 1 ) and 3‐amino‐2‐phenyl‐quinazolin‐4(3H)‐one ( 2 ) with (Ph)2PCl, PhPCl2, and PhP (O)Cl2 in different ratios. The synthesized compounds were characterized by elemental analysis and spectral tools. 相似文献
6.
Hui Huang Jian‐Fang Gao Ling‐Hua Cao Duo‐Zhi Wang Jian‐Bin Zhang Shu‐Bao Zhou Yu‐Qiang Zhou 《中国化学会会志》2009,56(2):419-424
A series of novel thioglycoside derivatives containing 4(3H)‐quinazolinone was designed and synthesized from 2‐chloromethyl‐quinazolin‐4(3H)‐ones and 1‐thioglycose. Several 2‐chloromethyl‐quinazolin‐4(3H)‐ones were synthesized on refluxing with 2‐(chloroacetylamino)‐benzoic acid and arylamines in acetonitrile. All of the novel compounds were characterized by IR, 1H NMR spectra and elemental analysis. The structures of compounds 7b, 8b and 8c have been determined by X‐ray diffraction analysis. 相似文献
7.
《Journal of heterocyclic chemistry》2018,55(2):517-521
Quinoxalino[2′,3′:5,6][1,3,4]thiadiazino[2,3‐b]quinazolin‐15‐one, a novel fused heterocyclic system, was synthesized from a one‐pot condensation reaction of 2,3‐dichloroquinoxaline and 3‐amino‐2‐thioxo‐2,3‐dihydroquinazolin‐4(1H)‐one under mild condition. Derivatization was performed on treatment of the titled compound with several alkyl bromides. In vitro antioxidant activity of the synthesized compounds was evaluated. 相似文献
8.
Manal M. Elshahawi Ahmed K. EL‐Ziaty Jehan M. Morsy Aly F. Aly 《Journal of heterocyclic chemistry》2016,53(5):1443-1448
A novel bis benzoxazin‐4‐one derivative has been synthesized and utilized to construct a new series of bis quinazolin‐4(3H)‐one derivatives via the reactions with different nitrogen nucleophiles namely, primary amines (ammonia, ethanolamine, and 4‐aminoantipyrine), secondary amines (morpholine and piperidine), diamine (o‐phenylenediamine), hydrazine hydrate, and hydroxylamine. The insecticidal efficacy of newly synthesized compounds was also studied. The structural features of the synthesized compounds were assigned by spectral analysis. 相似文献
9.
A new series of 2,3‐disubstituted quinazolin‐4(3H)‐one derivatives was synthesized by nucleophilic attack at C(2) of the corresponding key starting material 2‐propyl‐4H‐3,1‐benzoxazin‐4‐one (Scheme 2). The reaction proceeded via amidinium salt formation (Scheme 3) rather than via an N‐acylanthranilimide. The structure of the prepared compounds were elucidated by physical and spectral data like FT‐IR, 1H‐NMR, and mass spectroscopy. 相似文献
10.
M. S. Raghu C. B. Pradeep Kumar K. Yogesh Kumar M. K. Prashanth B. K. Jayanna 《Journal of heterocyclic chemistry》2019,56(7):2046-2051
A novel class of 3‐(4‐chlorophenyl)‐2‐(substituted)quinazolin‐4(3H)‐one derivatives were synthesized, and the structure of synthesized compounds was characterized by IR, 1H NMR, and mass spectroscopy. The newly synthesized compounds ( 4a–g and 6a–g ) were tested for their in vitro cyclooxygenase (COX) inhibition activity. The compounds have inhibitory profile against both COX‐1 and COX‐2, and some of the compounds are found to be selective against COX‐2. The compound 6g showed distinct inhibitory activity on COXs. The synthesized compounds were evaluated for their potential anti‐inflammatory activity as inhibitors of the proinflammatory cytokines IL‐6. Compounds 4d – g showed the highest level of inhibition among all the tested compounds. Thus, our data suggested that these compounds may represent a new class of potent anti‐inflammatory agents. 相似文献
11.
《Journal of heterocyclic chemistry》2017,54(6):3527-3537
Three new series of quinazolinone derivatives containing amide, urea, and sulfonamide were synthesized through multistep synthesis. The required intermediates 4‐[(4′‐oxo‐2,3,3′,4′,5,6‐hexahydro‐1′H ‐spiro[pyran‐4,2′‐quinazolin]‐1′‐yl)methyl]benzoic acid 4 and 1′‐(3‐aminobenzyl)‐2,3,5,6‐tetrahydro‐1′H ‐spiro[pyran‐4,2′‐quinazolin]‐4′(3′H )‐one 8 were prepared by hydrolysis of ester and reduction of nitro intermediates. Three different series of compounds were synthesized from these two scaffolds. The key scaffolds 4 and 8 were successfully converted to target molecules via amides 5a – k , urea 9a – f , and substituted sulfonamides 10a – e . The chemical structures of newly synthesized compounds were characterized by spectral analysis. The structure of 5d was confirmed by X‐ray crystallography study. These newly synthesized compounds were screened for antibacterial studies against Staphylococcus epidermidis , Salmonella typhi , Proteus mirabilis , and Shigella sonnei and for the antifungal activity against Aspergillus niger and Candida albicans . Among all the compounds, 9b – d showed excellent activities against S. typhi . Compound 9a showed moderate activity against all fungi stains, and 5I showed moderate activity against P. mirabilis , while the other derivatives showed fairly good activities. 相似文献
12.
Several 6‐substituted‐3‐[(5‐mercepto‐1,3,4‐oxadiazol‐2‐yl)methyl]‐2‐substituted quinazolin‐4(3H)‐one or 6‐substituted‐3‐[4‐(5‐mercepto‐1,3,4‐oxadiazol‐2‐yl)phenyl]‐2‐substituedquinazolin‐4(3H)‐one 2(a‐l) and 6‐substituted‐3‐[(5‐phenyl‐1,3,4‐oxadiazol‐2‐yl)methyl]‐2‐substitutedquinazolin‐4(3H)‐one or 6‐substi‐tuted‐3‐[4‐(5‐phenyl‐1,3,4‐oxadiazol‐2‐yl) phenyl]‐2‐substitutedquinazolin‐4(3H)‐one 3(a‐l) were synthesized using conventional and microwave techniques respectively and were screened for antibacterial and antifungal activity. 相似文献
13.
Mohammad Mahdavi Mehdi Asadi Mahsa Khoshbakht Mina Saeedi Mohammad Bayat Alireza Foroumadi Abbas Shafiee 《Helvetica chimica acta》2016,99(5):378-383
A series of novel quinazolin‐4(3H)‐one derivatives were efficiently synthesized starting from isatoic anhydride. First, reaction of isatoic anhydride and amines in H2O at room temperature afforded 2‐aminobenzamides. Then, CuBr/Et3N promoted reaction of 2‐aminobenzamides and different aryl isothiocyanates in DMF at 80° afforded the title compounds in good yield. 相似文献
14.
《Journal of heterocyclic chemistry》2018,55(7):1645-1650
2‐(Chloroseleno)benzoyl chloride serves as a versatile building block for the synthesis of novel ebselen (2‐phenyl‐1,2‐benzisoselenazol‐3(2H)‐one) analogues and benzo[b]selenophen‐3(2H)‐one derivatives. The antioxidant activity and cytotoxic evaluation of the newly synthesized compounds were implemented. Among all the synthesized compounds, 1‐(3‐hydroxybenzo[b]selenophen‐2‐yl)ethanone oxime ( 9 ) was the most potent antioxidant and the most cytotoxic compound as well. 相似文献
15.
《Journal of heterocyclic chemistry》2018,55(1):318-325
Presented article describes the synthesis and hypolipidemic activity of previously unknown 6,6‐disubstituted 3‐R‐6,7‐dihydro‐2H‐[1,2,4]triazino[2,3‐c]quinazolin‐2‐ones. It was shown, that interaction of 6‐R‐3‐(2‐aminophenyl)‐1,2,4‐triazin‐5(2Н)‐оnes with methylalkylketones in acetic acid resulted the single product, namely, the desired tricyclic derivatives. At the same time, after refluxing of 6‐R‐3‐(2‐aminophenyl)‐1,2,4‐triazin‐5(2Н)‐оnes with methylarylketones in acetic acid the mixture of target compound and insignificant amount of corresponding 3‐substituted 6‐methyl‐2H‐[1,2,4]triazino[2,3‐c]quinazolin‐2‐ones were isolated. The mechanism of above‐mentioned mixture formation was discussed. The structures of all synthesized compounds were proven using the appropriate physicochemical methods. The compounds with promising lipid‐lowering activity were identified and the «structure — hypolipidemic activity» correlations were discussed. 相似文献
16.
Reinvestigation of the Synthesis of Ketanserin (5) and its Hydrochloride Salt (5.HCl) via 3‐(2‐Chloroethyl)‐2,4‐(1H,3H)‐quinazolinedione (2) or Dihydro‐5H‐oxazole(2,3‐b)quinazolin‐5‐one (1)
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The synthesis of ketanserin ( 5 ) and its hydrochloride salt ( 5.HCl ) using respectively equimolar amounts of 3‐(2‐chloroethyl)‐2,4‐(1H,3H)‐quinazolinedione ( 2 ) with 4‐(parafluorobenzoyl)piperidine ( 3 ) and dihydro‐5H‐oxazole(2,3‐b)quinazolin‐5‐one ( 1 ) with hydrochloride salt of 4‐(parafluorobenzoyl)piperidine ( 3.HCl ) is reinvestigated. The one‐pot reaction of ethyl‐2‐aminobenzoate with ethyl chloroformate and ethanol amine has afforded 3‐(2‐chloroethyl)‐2,4‐(1H,3H)‐quinazolinedione ( 2 ) (86%) that was then refluxed with 4‐(parafluorobenzoyl)piperidine ( 3 ) in ethyl methyl ketone in the presence of sodium carbonate to obtain free base of ketanserin (87%). In another attempt, a very pure hydrochloride salt of ketanserin ( 5.HCl ) was synthesized using equimolar amounts of dihydro‐5H‐oxazole(2,3‐b)quinazolin‐5‐one ( 1 ) and hydrochloride salt of 4‐(parafluorobenzoyl)piperidine ( 3.HCl ) by a solvent‐less fusion method. Thus, under optimized conditions, 180°C and a reaction time of 30 min, the powder mixture was transformed into glassy crystals that were initially readily soluble in chloroform but were transformed afterwards over time (2 h) to white precipitates ( 5.HCl ) suspended in chloroform with a yield of 72%. 相似文献
17.
A Green Synthesis of Pyrrolo[1,2‐a]quinazolin‐5(1H)‐one Derivatives in Ionic Liquids Catalyzed by Iodine
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Jie‐Xing Zhou Lian Lu Tuan‐Jie Li Chang‐Sheng Yao Xiang‐Shan Wang 《Journal of heterocyclic chemistry》2014,51(5):1472-1475
A series of 2,3,3a,4‐tetrahydro‐3a‐methylpyrrolo[1,2‐a]quinazolin‐5(1H)‐one derivatives were synthesized by a reaction of 2‐aminobenzamide and 5‐chloropentan‐2‐one at 80 °C catalyzed by iodine in ionic liquid of [BMIm]Br. Compared with the other methods, this novel method has the advantages of milder reaction conditions, high yields, environmental benignity, and metal‐free catalyst. 相似文献
18.
Mahmoud. M. M. Ramiz Ibrahim. S. Abdel Hafiz Mohamed. A. M. Abdel Reheim Hatem M. Gaber 《中国化学会会志》2012,59(1):72-80
A series of new pyrazolone and pyrazole derivatives with expected antifungicidal activity have been prepared through the reactions 3‐phenyl‐1‐H‐pyrazol‐5(4H)‐one ( 3 ) and 4‐(dimethylaminomethylene)‐3‐phenyl‐1H‐pyrazol‐5(4H)‐one ( 5 ) with a variety of electrophilic reagents and nucleophilic reagents. The newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR and mass spectral studies. 相似文献
19.
《Journal of heterocyclic chemistry》2017,54(6):3187-3194
Sixteen Schiff bases of quinazolin‐4‐one‐linked 1,3,4‐oxadiazoles were synthesized by reaction with different aromatic aldehydes. Purity of newly synthesized derivatives was confirmed through thin‐layer chromatography, combustion analysis, and melting point. The structure of the derivatives was confirmed by determining infrared spectroscopy, nuclear magnetic resonance, and mass spectroscopy. All the synthesized derivatives were evaluated for their analgesic and anti‐inflammatory activities in mice and rats, respectively. In animal studies, the derivative (E )‐3‐(5‐(4‐(4‐methoxybenzylideneamino)phenyl)‐1,3,4‐oxadiazol‐2‐yl)‐2‐phenylquinazolin‐4(3H )‐one showed more potent analgesic activity and the derivative (Z )‐3‐(5‐(2‐(2‐hydroxybenzylideneamino)phenyl)‐1,3,4‐oxadiazol‐2‐yl)‐2‐phenylquinazolin‐4(3H )‐one showed more potent anti‐inflammatory activity as compared with other derivatives. The results of the present study indicate that reactions of 3‐(5‐(4‐aminophenyl)‐1,3,4‐oxadiazol‐2‐yl)‐2‐phenylquinazolin‐4(3H )‐one and 3‐(5‐(2‐aminophenyl)‐1,3,4‐oxadiazol‐2‐yl)‐2‐phenylquinazolin‐4(3H )‐one with different aromatic aldehydes produce Schiff bases of quinazolin‐4‐one‐linked 1,3,4‐oxadiazoles with potent analgesic and anti‐inflammatory activities. 相似文献
20.
Minhang Xin Ying Gao Hua Xiang Dong Chen Yi He Qidong You 《Journal of heterocyclic chemistry》2013,50(1):169-174
A simple and efficient approach to synthesize novel polysubstituted quinazolin‐4(3H)‐ones has been developed, and the key step is a sequential procedure involved iron‐mediated reduction and acid‐catalytic cyclization. The present method provides a convenient and practical strategy for the synthesis of quinazolin‐4(3H)‐one derivatives. 相似文献