Synthesis, antimicrobial, and mosquito larvicidal activity of 1-aryl-4-methyl-3,6-bis-(5-methylisoxazol-3-yl)-2-thioxo-2,3,6,10b-tetrahydro-1H-pyrimido[5,4-c]quinolin-5-ones

被引：85

作者：

Rajanarendar, E. ^{[1
]}

Reddy, M. Nagi ^{[1
]}

Murthy, K. Rama ^{[1
]}

Reddy, K. Govardhan ^{[1
]}

Raju, S. ^{[1
]}

Srinivas, M. ^{[1
]}

Praveen, B. ^{[2
]}

Rao, M. Srinivasa ^{[2
]}

机构：

[1] Kakatiya Univ, Dept Chem, Warangal 506009, Andhra Pradesh, India

[2] Indian Inst Chem Technol, Div Biol, Hyderabad 500007, Andhra Pradesh, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2010年 / 20卷 / 20期

关键词：

Isoxazolyl pyrimidoquinolines; Biginelli reaction; Antibacterial activity; Antifungal activity; Mosquito larvicidal test; ANTITUMOR-ACTIVITY; DERIVATIVES; ISOXAZOLES; ANTICANCER; INHIBITORS; DESIGN;

D O I：

10.1016/j.bmcl.2010.08.060

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of 1-aryl-4-methyl-3,6-bis-(5-methylisoxazol-3-yl)-2-thioxo-2,3,6,10b-tetrahydro-1H-pyrimido[5,4-c]quinolin-5-ones (6a-h) have been synthesized by cyclization of ethyl-3-aryl-4-(2-chlorophenyl)6-methyl- 1-(5- methylisoxazol-3-yl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates 4a-h with 3-amino-5-methylisoxazole5. Compounds 4a-h were obtained by Biginelli reaction, by condensation of aromatic aldehyde 1, ethyl acetoacetate 2, and isoxazolyl thioureas 3 in a one-pot reaction catalyzed by ceric ammonium nitrite (CAN). Compounds 6a-h were tested for their antibacterial and antifungal activities against various bacterial and fungal strains. The results showed that these compounds exhibited good antibacterial and antifungal activity compared with that of standard antibiotics. Mosquito larvicidal activity of the newly synthesized compounds 6a-h is also studied against fourth instar larvae Culex quinquefasciatus. Some of the compounds are proved to be lethal for mosquito larvae. (c) 2010 Elsevier Ltd. All rights reserved.

引用

页码：6052 / 6055

页数：4

共 50 条

[1] Synthesis of novel isoxazolo[2",3":1′,2′]pyrimido[4′,5′:4,5]pyrimido[6,1-b]quinazoline-8-ones and their in vitro anticancer and antimicrobial activities
Rajanarendar, E.
Kishore, B.
Ramakrishna, S.
Nagaraju, D.
Venkateshwarlu, P.
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2014, 53 (10): : 1275 - 1283
[2] MECHANOCHEMICAL SYNTHESIS OF ETHYL 4-(3-ARYL-1-PHENYL-1H-PYRAZOL-4-YL)-6-METHYL-2-OXO/THIOXO-1,2,3,4-TETRAHYDRO-PYRIMIDINE-5-CARBOXYLATES AND THEIR ANTIMICROBIAL ACTIVITY
Sarasija, M.
Ashok, D.
Sudershan, K.
Shivaraj
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 24 (03) : 349 - 352
[3] Chromatographic QSAR of 3-[ω-(4-Arylpiperazin-1-yl) alkyl] methylpyri-mido-[5,4-c] quinolin-4(3H)-ones for the 5-HT1A Receptor Characterization
Lewgowd, Wieslawa
Szumilak, Marta
Zydek, Grazyna
CURRENT ANALYTICAL CHEMISTRY, 2016, 12 (06) : 537 - 544
[4] Synthesis and antimicrobial activity of novel 5-methyl-1-(4-(6-methylimidazo [1,2-b]isoxazol-3-yl)phenyl)-3-aryl-1,3,5-triazinane-2-thiones
Marri, Srinivas
INDIAN JOURNAL OF CHEMISTRY, 2022, 61 (10): : 1046 - 1053
[5] Synthesis of novel bis(pyrimido[5,4-c]quinoline-2,4(1H,3H)-dione) and its derivatives: Evaluation of their antioxidant properties
Parameswaran, Kandasamy
Sivaguru, Paramasivam
Lalitha, Appaswami
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (13) : 3873 - 3878
[6] Synthesis of 5,5-(ethane-1,2-diyl)bis(3-((5-bromo-6-methyl-2-tertiaryaminopyrimidin-4-yl)thio)-4H-1,2,4-triazol-4-amines) and Their Novel bis-cyclized Products, 1,2-bis(pyrimido[5,4e][1,2,4] triazolo[3,4-b][1,3,4]thiadiazin-3-yl)ethane, as Potential Inhibitors of 15-Lipoxygenase
Asghari, Tayebe
Bakavoli, Mehdi
Eshghi, Hossein
Saberi, Sattar
Ebrahimpour, Zahra
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (02) : 403 - 407
[7] Synthesis and Antimicrobial Activities of (4,5,6,7-Tetrahydro-1H-indazol-2(3H)-yl)thiazole Derivatives
Laczkowski, Krzysztof Z.
Misiura, Konrad
Biernasiuk, Anna
Malm, Anna
LETTERS IN DRUG DESIGN & DISCOVERY, 2014, 11 (08) : 960 - 967
[8] Catalytic synthesis and antimicrobial activity of N-(3-chloro-2-oxo-4-phenylazetidin-1-yl)-4-(1H-indol-3-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides
Desai, Nisheeth C.
Bhatt, Malay J.
HETEROCYCLIC COMMUNICATIONS, 2016, 22 (03) : 131 - 136
[9] Synthesis and anticancer activity of 3-(1-aryl-5-methyl-1H-1,2 3-triazol-4-yl)-1-phenyl-1H-pyrazole-4-carbaldehydes
Abdel-Wahab, Bakr F.
Kariuki, Benson M.
Mohamed, Hanan A.
Bekheit, Mohamed S.
Awad, Hanem M.
El-Hiti, Gamal A.
JOURNAL OF MOLECULAR STRUCTURE, 2023, 1294
[10] Synthesis and Antimicrobial Activity of Bis[4-methoxy-3-(6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)phenyl]methanes and Bis[(triazolo[3,4-b]thiadiazepin-3-yl)phenyl]methanes
Srinivas, Avula
ACTA CHIMICA SLOVENICA, 2016, 63 (01) : 173 - 179

← 1 2 3 4 5 →