一种高效微波辅助合成新型若丹宁衍生物作为潜在HIV-1和JSP-1抑制剂的方法。
An efficient microwave assisted synthesis of novel class of Rhodanine derivatives as potential HIV-1 and JSP-1 inhibitors.
作者信息
Kamila Sukanta, Ankati Haribabu, Biehl Edward R
机构信息
Southern Methodist University, Department of, Chemistry, Dallas, TX, 75275.
出版信息
Tetrahedron Lett. 2011 Aug 24;52(34):4375-4377. doi: 10.1016/j.tetlet.2011.05.114.
Abstract
(Z)-5-(2-(1H-Indol-3-yl)-2-oxoethylidene)-3-phenyl-2-thioxothiazolidin-4-one (7a-q) derivatives have been synthesized by the condensation reaction of 3-phenyl-2-thioxothiazolidin-4-ones (3a-h) with suitably substituted 2-(1H-indol-3-yl)-2-oxoacetaldehyde (6a-d) under microwave condition. The thioxothiazolidine-4-ones were prepared from corresponding aromatic amines (1a-e) and di-(carboxymethyl)-trithiocarbonyl (2). The aldehydes (6a-h) were synthesized from the corresponding acidchlorides (5a-d) using HSnBu(3).
摘要
通过3-苯基-2-硫代噻唑烷-4-酮（3a-h）与适当取代的2-（1H-吲哚-3-基）-2-氧代乙醛（6a-d）在微波条件下缩合反应，合成了（Z）-5-（2-（1H-吲哚-3-基）-2-氧代亚乙基）-3-苯基-2-硫代噻唑烷-4-酮（7a-q）衍生物。硫代噻唑烷-4-酮由相应的芳香胺（1a-e）和二（羧甲基）三硫代羰基（2）制备。醛（6a-h）由相应的酰氯（5a-d）使用三丁基氢化锡（HSnBu(3)）合成。
相似文献
1
An efficient microwave assisted synthesis of novel class of Rhodanine derivatives as potential HIV-1 and JSP-1 inhibitors.一种高效微波辅助合成新型若丹宁衍生物作为潜在HIV-1和JSP-1抑制剂的方法。
Tetrahedron Lett. 2011 Aug 24;52(34):4375-4377. doi: 10.1016/j.tetlet.2011.05.114.
2
Synthesis of novel 2-amino-4-(5'-substituted 2'-phenyl-1H-indol-3'-yl)-6-aryl-4H-pyran-3-carbonitrile derivatives as antimicrobial and antioxidant agents.合成新型 2-氨基-4-(5'-取代-2'-苯基-1H-吲哚-3'-基)-6-芳基-4H-吡喃-3-甲腈衍生物作为抗菌和抗氧化剂。
Bioorg Med Chem Lett. 2013 Apr 1;23(7):1978-84. doi: 10.1016/j.bmcl.2013.02.036. Epub 2013 Feb 16.
3
Synthesis, pharmacological screening and computational analysis of some 2-(1H-Indol-3-yl)-N'-[(un)substituted phenylmethylidene] acetohydrazides and 2-(1H-Indol-3-yl)-N'-[(un)substituted benzoyl/2-thienylcarbonyl]acetohydrazides.某些2-(1H-吲哚-3-基)-N'-[(未)取代的苯基亚甲基]乙酰肼和2-(1H-吲哚-3-基)-N'-[(未)取代的苯甲酰基/2-噻吩羰基]乙酰肼的合成、药理筛选及计算分析
Pak J Pharm Sci. 2017 Jul;30(4):1263-1274.
4
Microwave assisted synthesis of novel functionalized hydantoin derivatives and their conversion to 5-(Z) arylidene-4H-imidazoles.微波辅助合成新型功能化海因衍生物及其转化为 5-(Z)-芳基亚甲基-4H-咪唑。
Molecules. 2011 Jun 29;16(7):5527-37. doi: 10.3390/molecules16075527.
5
Microwave-assisted Hantzsch thiazole synthesis of N-phenyl-4-(6-phenylimidazo[2,1-b]thiazol-5-yl)thiazol-2-amines from the reaction of 2-chloro-1-(6-phenylimidazo[2,1-b]thiazol-5-yl)ethanones and thioureas.通过2-氯-1-(6-苯基咪唑并[2,1-b]噻唑-5-基)乙酮与硫脲反应，微波辅助汉茨希噻唑合成N-苯基-4-(6-苯基咪唑并[2,1-b]噻唑-5-基)噻唑-2-胺。
Tetrahedron Lett. 2012 Sep 12;53(37):4921-4924. doi: 10.1016/j.tetlet.2012.06.116. Epub 2012 Jul 3.
6
Synthesis, anticonvulsant and toxicity evaluation of 2-(1H-indol-3-yl)acetyl-N-(substituted phenyl)hydrazine carbothioamides and their related heterocyclic derivatives.2-(1H-吲哚-3-基)乙酰基-N-(取代苯基)肼基硫代甲酰胺及其相关杂环衍生物的合成、抗惊厥活性及毒性评价
Acta Pharm. 2008 Dec;58(4):445-54. doi: 10.2478/v10007-008-0025-0.
7
Facile one pot microwave induced solvent-free synthesis and antifungal, antitubercular screening of spiro [1,5]-benzothiazepin-2,3'[3'H]indol-2[1'H]-ones.
Chem Pharm Bull (Tokyo). 2003 Oct;51(10):1137-41. doi: 10.1248/cpb.51.1137.
8
Synthesis and potential biological activity of some novel 3-[(N-substituted indol-3-yl)methyleneamino]-6-amino-4-aryl-pyrano(2,3-c)pyrazole-5-carbonitriles and 3,6-diamino-4-(N-substituted indol-3-yl)pyrano(2,3-c)pyrazole-5-carbonitriles.一些新型 3-[(N-取代吲哚-3-基)亚甲基氨基]-6-氨基-4-芳基-吡喃(2,3-c)吡唑-5-甲腈和 3,6-二氨基-4-(N-取代吲哚-3-基)吡喃(2,3-c)吡唑-5-甲腈的合成及潜在生物活性。
Acta Pharm. 2012 Mar;62(1):15-30. doi: 10.2478/v10007-012-0007-0.
9
Microwave assisted condensation reactions of 2-aryl hydrazonopropanals with nucleophilic reagents and dimethyl acetylenedicarboxylate.2-芳基肼基丙醛与亲核试剂及乙酰基二羧酸二甲酯的微波辅助缩合反应
Molecules. 2007 Aug 24;12(8):2061-79. doi: 10.3390/12082061.
10
Synthesis and Antimicrobial Activity of 2-[2-(2,6-dichloro phenyl)amino]benzyl-3-(5-substituted phenyl-4,5-dihydro-1H-pyrazol-3-yl-amino)-6,8-dibromoquinazolin-4(3H)ones.2-[2-(2,6-二氯苯基)氨基]苄基-3-(5-取代苯基-4,5-二氢-1H-吡唑-3-基氨基)-6,8-二溴喹唑啉-4(3H)酮的合成与抗菌活性
J Young Pharm. 2010 Apr;2(2):173-82. doi: 10.4103/0975-1483.63165.
引用本文的文献
1
Advances in the synthesis of nitrogen-containing heterocyclic compounds by benzyne cycloaddition.通过苯炔环加成反应合成含氮杂环化合物的研究进展。
RSC Adv. 2023 Mar 13;13(12):8238-8253. doi: 10.1039/d3ra00400g. eCollection 2023 Mar 8.
2
Development of a Novel Series of Anticancer and Antidiabetic: Spirothiazolidines Analogs.新型抗癌和抗糖尿病螺噻唑烷二酮类化合物的开发。
Molecules. 2019 Jul 9;24(13):2511. doi: 10.3390/molecules24132511.
3
Structural analysis of human dual-specificity phosphatase 22 complexed with a phosphotyrosine-like substrate.与磷酸酪氨酸样底物复合的人双特异性磷酸酶22的结构分析。
Acta Crystallogr F Struct Biol Commun. 2015 Feb;71(Pt 2):199-205. doi: 10.1107/S2053230X15000217. Epub 2015 Jan 28.
4
A simple and green procedure for the synthesis of 5-arylidenerhodanines catalyzed by diammonium hydrogen phosphate in water.一种在水中由磷酸氢二铵催化合成5-芳亚甲基绕丹宁的简单绿色方法。
ScientificWorldJournal. 2013 Oct 22;2013:543768. doi: 10.1155/2013/543768. eCollection 2013.
5
Microwave-assisted Hantzsch thiazole synthesis of N-phenyl-4-(6-phenylimidazo[2,1-b]thiazol-5-yl)thiazol-2-amines from the reaction of 2-chloro-1-(6-phenylimidazo[2,1-b]thiazol-5-yl)ethanones and thioureas.通过2-氯-1-(6-苯基咪唑并[2,1-b]噻唑-5-基)乙酮与硫脲反应，微波辅助汉茨希噻唑合成N-苯基-4-(6-苯基咪唑并[2,1-b]噻唑-5-基)噻唑-2-胺。
Tetrahedron Lett. 2012 Sep 12;53(37):4921-4924. doi: 10.1016/j.tetlet.2012.06.116. Epub 2012 Jul 3.
6
Parallel solid-phase synthesis of diaryltriazoles.联芳基三氮唑的平行固相合成。
Beilstein J Org Chem. 2012;8:1027-36. doi: 10.3762/bjoc.8.115. Epub 2012 Jul 6.
7
Three-component, one-flask synthesis of rhodanines (thiazolidinones).三组分一锅法合成罗哒宁（噻唑烷酮）。
J Org Chem. 2011 Oct 7;76(19):8121-5. doi: 10.1021/jo201561t. Epub 2011 Aug 31.
8
Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.2009年药物发现与化学生物学化学文库综合调查
J Comb Chem. 2010 Nov 8;12(6):765-806. doi: 10.1021/cc100128w. Epub 2010 Oct 5.
本文引用的文献
1
Design, synthesis, and biological activity of novel 5-((arylfuran/1H-pyrrol-2-yl)methylene)-2-thioxo-3-(3-(trifluoromethyl)phenyl)thiazolidin-4-ones as HIV-1 fusion inhibitors targeting gp41.新型 5-((芳基呋喃基/1H-吡咯-2-基)亚甲基)-2-硫代-3-(3-(三氟甲基)苯基)噻唑烷-4-酮作为靶向 HIV-1 融合蛋白 gp41 的抑制剂的设计、合成与活性
J Med Chem. 2011 Jan 27;54(2):572-9. doi: 10.1021/jm101014v. Epub 2010 Dec 29.
2
Identification of novel 1,4-benzoxazine compounds that are protective in tissue culture and in vivo models of neurodegeneration.鉴定在神经退行性变的组织培养和体内模型中具有保护作用的新型 1,4-苯并恶嗪化合物。
J Neurosci Res. 2010 Jul;88(9):1970-84. doi: 10.1002/jnr.22352.
3
Straightforward synthesis of the near-infrared fluorescent voltage-sensitive dye RH1691 and analogues thereof.
Org Lett. 2009 Nov 5;11(21):4822-5. doi: 10.1021/ol901846g.
4
Fascaplysin-inspired diindolyls as selective inhibitors of CDK4/cyclin D1.受法斯卡普林启发的二吲哚类化合物作为CDK4/细胞周期蛋白D1的选择性抑制剂
Bioorg Med Chem. 2009 Aug 15;17(16):6073-84. doi: 10.1016/j.bmc.2009.06.070. Epub 2009 Jul 12.
5
Synthesis and structure-activity relationship studies of 3-substituted indolin-2-ones as effective neuroprotective agents.作为有效神经保护剂的3-取代吲哚啉-2-酮的合成及其构效关系研究
Exp Biol Med (Maywood). 2008 Nov;233(11):1395-402. doi: 10.3181/0805-RM-153.
6
Rhodanine derivatives as inhibitors of JSP-1.作为JSP-1抑制剂的若丹宁衍生物
Bioorg Med Chem Lett. 2005 Jul 15;15(14):3374-9. doi: 10.1016/j.bmcl.2005.05.034.
7
Novel 5-HT7 receptor inverse agonists. Synthesis and molecular modeling of arylpiperazine- and 1,2,3,4-tetrahydroisoquinoline-based arylsulfonamides.新型5-HT7受体反向激动剂。基于芳基哌嗪和1,2,3,4-四氢异喹啉的芳基磺酰胺的合成与分子模拟。
J Med Chem. 2004 Oct 21;47(22):5451-66. doi: 10.1021/jm049743b.
8
The prevalence of antiretroviral drug resistance in the United States.美国抗逆转录病毒药物耐药性的流行情况。
AIDS. 2004 Jul 2;18(10):1393-401. doi: 10.1097/01.aids.0000131310.52526.c7.
9
Antiviral drugs in current clinical use.当前临床使用的抗病毒药物。
J Clin Virol. 2004 Jun;30(2):115-33. doi: 10.1016/j.jcv.2004.02.009.
10
Drug resistance mutations in HIV-1.HIV-1中的耐药性突变
Top HIV Med. 2003 Nov-Dec;11(6):215-21.
Zotero 插件