合成、表征和 1H-吡唑碳氮杂环丁烷衍生物的抗菌评价。
Synthesis, characterization, and antimicrobial evaluation of carbostyril derivatives of 1H-pyrazole.
机构信息
Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, 388120 Gujarat, India.
出版信息
Saudi Pharm J. 2011 Apr;19(2):75-83. doi: 10.1016/j.jsps.2011.01.005. Epub 2011 Feb 3.
Abstract
A new series of 12 derivatives of 4-pyrazolyl-N-arylquinoline-2,5-dione (4a-l) were synthesized by one pot base catalyzed cyclocondensation reaction of 1-aryl-5-chloro-3-methyl-1H-pyrazole-4-carbaldehyde (1a-c), Meldrum's acid (2) and 3-arylamino-5,5-disubstitutedcyclohex-2-enone (3a-d). All the compounds were characterized by elemental analysis, FT-IR, (1)H NMR and (13)C NMR spectral data and were screened, against six bacterial pathogens, namely Bacillus subtilis, Clostridium tetani, Streptococcus pneumoniae, Salmonella typhi, Vibrio cholerae, Escherichia coli and antifungal activity, against two fungal pathogens Aspergillus fumigatus and Candida albicans, using broth microdilution MIC (minimum inhibitory concentration) method. Some of the compounds were found to be equipotent or more potent than commercial drugs, against most of the employed strains, as evident from the screening data.
摘要
通过一锅碱催化缩合反应，将 1-芳基-5-氯-3-甲基-1H-吡唑-4-甲醛（1a-c）、Meldrum's 酸（2）和 3-芳基氨基-5,5-二取代环己-2-烯酮（3a-d）合成了一系列 12 种新的 4-吡唑基-N-芳基喹啉-2,5-二酮（4a-l）衍生物。所有化合物均通过元素分析、FT-IR、（1）H NMR 和（13）C NMR 光谱数据进行了表征，并通过微量肉汤稀释法（最小抑菌浓度，MIC）对其进行了抗六种细菌病原体（枯草芽孢杆菌、破伤风梭菌、肺炎链球菌、伤寒沙门氏菌、霍乱弧菌和大肠杆菌）和两种真菌病原体（烟曲霉和白色念珠菌）的活性筛选。从筛选数据可以看出，一些化合物在大多数试验菌株中与商业药物相当或更有效。
相似文献
1
Synthesis, characterization, and antimicrobial evaluation of carbostyril derivatives of 1H-pyrazole.合成、表征和 1H-吡唑碳氮杂环丁烷衍生物的抗菌评价。
Saudi Pharm J. 2011 Apr;19(2):75-83. doi: 10.1016/j.jsps.2011.01.005. Epub 2011 Feb 3.
2
Synthesis and antimicrobial activity of some new N-substituted quinoline derivatives of 1H-pyrazole.合成及一些新的 N-取代的 1H-吡唑基喹啉衍生物的抗菌活性。
Arch Pharm (Weinheim). 2011 Feb;344(2):91-101. doi: 10.1002/ardp.201000010. Epub 2010 Dec 22.
3
Synthesis and antimicrobial evaluation of new pyrano[4,3-b]pyran and Pyrano[3,2-c]chromene derivatives bearing a 2-thiophenoxyquinoline nucleus.新型含 2-噻吩氧基喹啉核的吡喃并[4,3-b]吡喃和吡喃并[3,2-c]色烯衍生物的合成及抗菌评价。
Arch Pharm (Weinheim). 2012 Apr;345(4):314-22. doi: 10.1002/ardp.201100203. Epub 2011 Nov 22.
4
Antimicrobial and cytotoxic activities of isoniazid connected menthone derivatives and their investigation of clinical pathogens causing infectious disease.异烟肼连接的薄荷酮衍生物的抗菌和细胞毒性活性及其对引起传染病的临床病原体的研究。
J Infect Public Health. 2021 Apr;14(4):533-542. doi: 10.1016/j.jiph.2020.12.033. Epub 2021 Feb 6.
5
Microwave assisted synthesis and antimicrobial evaluation of new fused pyran derivatives bearing 2-morpholinoquinoline nucleus.微波辅助合成及含 2-吗啉基喹啉核的新型稠合吡喃衍生物的抗菌评价。
Bioorg Med Chem Lett. 2011 Oct 15;21(20):6166-9. doi: 10.1016/j.bmcl.2011.07.123. Epub 2011 Aug 6.
6
Synthesis of new thiazolyl-pyrazolyl-1,2,3-triazole derivatives as potential antimicrobial agents.合成新型噻唑基-吡唑基-1,2,3-三唑衍生物作为潜在的抗菌剂。
Eur J Med Chem. 2019 Oct 1;179:649-659. doi: 10.1016/j.ejmech.2019.06.074. Epub 2019 Jun 27.
7
Antimicrobial screening and one-pot synthesis of 4-(substituted-anilinomethyl)-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives.4-(取代苯胺甲基)-3-(2-萘基)-1-苯基-1H-吡唑衍生物的抗菌筛选及一锅法合成
J Pharm Bioallied Sci. 2014 Oct;6(4):253-9. doi: 10.4103/0975-7406.142956.
8
Synthesis, characterization and antimicrobial activity of a novel chitosan Schiff bases based on heterocyclic moieties.新型基于杂环结构的壳聚糖希夫碱的合成、表征及抗菌活性研究。
Int J Biol Macromol. 2020 Jun 15;153:492-501. doi: 10.1016/j.ijbiomac.2020.02.302. Epub 2020 Feb 26.
9
Synthesis and Biological Screening of New 2-(5-Aryl-1-phenyl-1-pyrazol-3-yl)-4-aryl Thiazole Derivatives as Potential Antimicrobial Agents.新型2-(5-芳基-1-苯基-1-吡唑-3-基)-4-芳基噻唑衍生物作为潜在抗菌剂的合成与生物学筛选
ACS Omega. 2023 Feb 22;8(9):8743-8754. doi: 10.1021/acsomega.2c08137. eCollection 2023 Mar 7.
10
Synthesis and identification of β-aryloxyquinolines and their pyrano[3,2-c]chromene derivatives as a new class of antimicrobial and antituberculosis agents.β-芳氧基喹啉及其吡喃并[3,2-c]色烯衍生物的合成与鉴定作为一类新型的抗菌和抗结核药物。
Eur J Med Chem. 2011 Sep;46(9):4192-200. doi: 10.1016/j.ejmech.2011.06.022. Epub 2011 Jun 23.
引用本文的文献
1
Synthesis and anti-breast cancer evaluation of novel N-(guanidinyl)benzenesulfonamides.新型N-（胍基）苯磺酰胺的合成及抗乳腺癌评估
Int J Mol Sci. 2014 Apr 1;15(4):5582-95. doi: 10.3390/ijms15045582.
2
3-Acetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile.3-乙酰基-1,5-二苯基-1H-吡唑-4-腈
Acta Crystallogr Sect E Struct Rep Online. 2012 Apr 1;68(Pt 4):o1095-6. doi: 10.1107/S1600536812010938. Epub 2012 Mar 17.
3
5,6-Dimethyl-4-(thio-phen-2-yl)-1H-pyrazolo-[3,4-b]pyridin-3-amine.5,6-二甲基-4-(噻吩-2-基)-1H-吡唑并-[3,4-b]吡啶-3-胺
Acta Crystallogr Sect E Struct Rep Online. 2012 Mar 1;68(Pt 3):o612-3. doi: 10.1107/S1600536812004126. Epub 2012 Feb 4.
本文引用的文献
1
Synthesis and antimicrobial activity of some new N-substituted quinoline derivatives of 1H-pyrazole.合成及一些新的 N-取代的 1H-吡唑基喹啉衍生物的抗菌活性。
Arch Pharm (Weinheim). 2011 Feb;344(2):91-101. doi: 10.1002/ardp.201000010. Epub 2010 Dec 22.
2
Synthesis and antimicrobial activity of some new pyrazole derivatives containing a ferrocene unit.一些含二茂铁单元的新型吡唑衍生物的合成与抗菌活性
Bioorg Med Chem Lett. 2009 Feb 15;19(4):1093-6. doi: 10.1016/j.bmcl.2009.01.006. Epub 2009 Jan 9.
3
The structure of Meldrum's supposed beta-lactonic acid.梅尔德伦假定的β-内酯酸的结构。
J Am Chem Soc. 1948 Oct;70(10):3426-8. doi: 10.1021/ja01190a060.
4
Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloro-quinolin-2-one and 5-aryl-7-chloro-1,4-benzodiazepine derivatives.4-芳基-6-氯喹啉-2-酮和5-芳基-7-氯-1,4-苯并二氮杂卓衍生物的合成及其体外抗乙型肝炎病毒活性
Bioorg Med Chem Lett. 2008 Jul 1;18(13):3787-9. doi: 10.1016/j.bmcl.2008.05.065. Epub 2008 May 20.
5
Implications for selectivity of 3,4-diarylquinolinones as p38alphaMAP kinase inhibitors.3,4-二芳基喹啉酮作为p38α丝裂原活化蛋白激酶抑制剂的选择性影响
Bioorg Med Chem Lett. 2008 Feb 15;18(4):1431-5. doi: 10.1016/j.bmcl.2007.12.073. Epub 2008 Jan 5.
6
Synthesis of potential Rho-kinase inhibitors based on the chemistry of an original heterocycle: 4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one.基于一种原始杂环化合物（4,4-二甲基-3,4-二氢-1H-喹啉-2-酮）化学结构的潜在Rho激酶抑制剂的合成。
Eur J Med Chem. 2008 Aug;43(8):1730-6. doi: 10.1016/j.ejmech.2007.11.010. Epub 2007 Nov 23.
7
Synthesis, antiproliferative, and antiplatelet activities of oxime- and amide-containing quinolin-2(1H)-one derivatives.含肟和酰胺基喹啉-2(1H)-酮衍生物的合成、抗增殖及抗血小板活性
Bioorg Med Chem. 2007 Oct 15;15(20):6527-34. doi: 10.1016/j.bmc.2007.07.007. Epub 2007 Jul 26.
8
Synthesis and biological evaluation of some thiazolyl and thiadiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial agents.1H-吡唑的一些噻唑基和噻二唑基衍生物作为抗炎抗菌剂的合成及生物学评价
Eur J Med Chem. 2008 Mar;43(3):456-63. doi: 10.1016/j.ejmech.2007.03.030. Epub 2007 Apr 14.
9
Conversion of some 2(3H)-furanones bearing a pyrazolyl group into other heterocyclic systems with a study of their antiviral activity.将一些带有吡唑基的2(3H)-呋喃酮转化为其他杂环体系并研究其抗病毒活性。
Eur J Med Chem. 2007 Jul;42(7):934-9. doi: 10.1016/j.ejmech.2006.12.032. Epub 2007 Jan 14.
10
Discovery of an androgen receptor modulator pharmacophore based on 2-quinolinones.基于2-喹啉酮的雄激素受体调节剂药效团的发现。
Bioorg Med Chem Lett. 2007 Mar 15;17(6):1523-6. doi: 10.1016/j.bmcl.2007.01.007. Epub 2007 Jan 13.
Zotero 插件