CAS: 5470-96-2; Quinoline-2-Carboxaldehyde

该化合物是一种在有机合成和制药研究中广泛使用的多功能性七环甲醚. 其quinoline主脊椎具有独特的电子特性,使其成为构建复杂分子,包括离子,催化剂和生物活性化合物的宝贵中间体. 位于2位置的甲功能组为凝聚,减少和核循环添加反应提供了反应的再活性,允许多种衍生. 该化合物在药用化学中特别有用,用于开发抗微生物和抗突触剂,因为它在结构上与药用活性等离子衍生物相似. 高纯度可以确保敏感应用的一贯性能. 其稳定性和精细化性再活性剖面使其成为合成工作流程的可靠选择.

结构式图片

相似化合物

19575-07-6 93-10-7 1436-43-7

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上下游产品

CAS号91-63-4 2-甲基喹啉 | CAS号2005-43-8 2-溴喹啉 | CAS号201230-82-2 carbon monoxide | CAS号109586-44-9 trifluoromethan... | CAS号5330-88-1 2-(pyridin-1-yl... | CAS号67-56-1 甲醇 | CAS号1335204-96-0 quinolin-2-yl(b... | CAS号53867-81-5 2-(二溴甲基)喹啉 | CAS号4377-41-7 2-(氯甲基)喹啉 | CAS号79-46-9 2-硝基丙烷 | CAS号5632-15-5 2-溴甲基喹啉 | CAS号4491-33-2 2-喹啉甲酸乙酯 | CAS号235-21-2 [1,2,3]TRIAZOLO... | CAS号24613-96-5 2-quinolin-2-yl... | CAS号24613-99-8 2-Benzothiazol-... | CAS号24640-96-8 N-(4-chlorophen... | CAS号76532-33-7 N-甲基-2-萘甲胺 | CAS号772-03-2 2-乙烯基喹啉 | CAS号14044-48-5 2-(1H-苯并[d]咪唑-2-基)喹啉 | CAS号93-10-7 喹哪啶酸

合成工艺路线路线简述

  • 合成目标产物 2-Quinolinecarboxaldehyde 主要起始原料 Ethyl Quinoline-2-Carboxylate
  • (文献来源)合成步骤主要原料 Ethyl Quinoline-2-Carboxylate
4-羟基-2-甲基喹啉置于selenium(Iv) Oxide,正丁基锂,三溴化磷体系中,用 四氢呋喃,1,4-二氧六环,N,N-二甲基甲酰胺 作为反应溶剂,化学反应 5.5H,反应生成 喹啉-2-甲醛
参考文献:设计,合成和生物评价2-取代喹啉作为潜在的抗疟药
标题:设计,合成和生物评价2-取代喹啉作为潜在的抗疟药
摘要:为了确定潜在的候选药物治疗内脏利什曼病,合成了2-取代的喹啉化合物的类似物库.测试了这些分子对利什曼原虫的体外和体内生物活性.这些化合物的代谢稳定性也通过引入卤素取代基得到了改善.化合物(26G),被发现是最活跃的;ic 50值为0.2μm,选择性> 180倍.(26G)的盐酸盐在l. Donovani中50 Mg / Kgx5天(每天两次,口服)剂量下显示84.26+/-4.44%的抑制作用/仓鼠模型.功效与观测到的pk数据高度相关,这表明该化合物分布均匀.
DOI:10.1016/j.Ejmech.2013.08.028

海关参考信息

专利信息


专利号:US-5877278-A
优先权日:1992-09-24
标题:Synthesis of N-substituted oligomers
发明人:ZUCKERMANN RONALD N; GOFF DANE A; NG SIMON; SPEAR KERRY; SCOTT BARBARA O; SIGMUND AARON C; GOLDSMITH RICHARD A; MARLOWE CHARLES K; PEI YAZHONG; RICHTER LUTZ; SIMON REYNA
权利人:CHIRON CORP
摘要:A solid-phase method for the synthesis of N-substituted oligomers, such as poly (N-substituted glycines) (referred to herein as poly NSGs) is used to obtain oligomers, such as poly NSGs of potential therapeutic interest which poly NSGs can have a wide variety of side-chain substituents. Each N-substituted glycine monomer is assembled from two 'sub-monomers' directly on the solid support. Each cycle of monomer addition consists of two steps: (1) acylation of a secondary amine bound to the support with an acylating agent comprising a leaving group capable of nucleophilic displacement by -NH2, such as a haloacetic acid, and (2) introduction of the side-chain by nucleophilic displacement of the leaving group, such as halogen (as a solid support-bound alpha -haloacetamide) with a sufficient amount of a second sub-monomer comprising an -NH2 group, such as a primary amine, alkoxyamine, semicarbazide, acyl hydrazide, carbazate or the like. Repetition of the two step cycle of acylation and displacement gives the desired oligomers. The efficient synthesis of a wide variety of oligomeric NSGs using automated synthesis technology of the present method makes these oligomers attractive candidates for the generation and rapid screening of diverse peptidomimetic libraries. The oligomers of the invention, such as N-substituted glycines (i.e. poly NSGs) disclosed here provide a new class of peptide-like compounds not found in nature, but which are synthetically accessible and have been shown to possess significant biological activity and proteolytic stability. Combinatorial libraries of cyclic compounds are disclosed wherein the cyclic compounds are comprised of at least one ring structure derived from cyclization of a peptoid backbone. The diversity of product compounds is generated by the sequential addition of substituted submonomers. The combinatorial library includes 10 or more, preferably 100 or more, and more preferably 1,000 or more distinct and different compounds. The library includes each of the product compounds in retrievable and analyzable amounts and preferably includes at least one biologically active compound. Methods of synthesizing the combinatorial libraries and assay devices produced using the libraries are disclosed as is methodology for screening for and obtaining biologically active cyclic organic compounds.

专利号:US-2007293456-A9
优先权日:2004-12-30
标题:Method for the synthesis of 3-substituted indolizine and benzoindolizine compounds
发明人:HAYFORD ANTHONY; KALOKO JOSEPH
权利人:HAYFORD ANTHONY; KALOKO JOSEPH
摘要:A method of making a compound of Formula I: n n ncomprises reacting a compound of Formula II n n nwith a compound such as R 1 OH or R 1 SH, to produce said compound of Formula I. Compounds of Formula I are useful, among other things, as dyes, spectral sensitizers, glycosidase inhibitors, and as antibacterial, antiviral, and anti-inflammatory agents.

专利号:US-7339065-B2
优先权日:2003-07-21
标题 :Design and synthesis of optimized ligands for PPAR
发明人:AVERY MITCHELL A; PERSHADSINGH HARRIHAR A
权利人:BETHESDA PHARMACEUTICALS INC; UNIV MISSISSIPPI
摘要:This invention provides new chemical entities useful for treating a variety of clinical disorders including those that are influenced by the activity of peroxisome proliferator activated receptors (PPAR). The structures of the compounds and methods to design, make and use the compounds are provided. Compounds and methods for administering therapeutic compositions comprising the compounds in cases of the disease psoriasis are provided. An exemplary compound having the formula compound is 5adamantan-2-yl-pentanoic acid {2-[4-(2,4-dioxo-thiazolidin-5-yl-methyl)-phenoxy]-ethyl}-methyl-amide is provided.

专利号:US-7074932-B2
优先权日:1999-06-24
标题 :Preparation of quinoline-substituted carbonate and carbamate derivatives
发明人:ALLEN MICHAEL S; PREMCHANDRAN RAMIYA H; CHANG SOU-JEN; CONDON STEPHEN; DEMATTEI JOHN A; KING STEVEN A; KOLACZKOWSKI LAWRENCE; MANNA SUKUMAR; NICHOLS PAUL J; PATEL HEMANT H; PATEL SUBHASH R; PLATA DANIEL J; STONER ERIC J; TIEN JIEN-HEH J; WITTENBERGER STEVEN J
权利人:ALLEN MICHAEL S; PREMCHANDRAN RAMIYA H; CHANG SOU-JEN; CONDON STEPHEN; DEMATTEI JOHN A; KING STEVEN A; KOLACZKOWSKI LAWRENCE; MANNA SUKUMAR; NICHOLS PAUL J; PATEL HEMANT H; PATEL SUBHASH R; PLATA DANIEL J; STONER ERIC J; TIEN JIEN-HEH J; WITTENBERGER STEVEN J
摘要:The invention relates to a process for preparing quinoline-substituted carbonate and carbamate compounds, which are important intermediates in the synthesis of 6-O-substituted macrolide antibiotics. The process employs metal-catalyzed coupling reactions to provide a carbonate or carbamate of formula (I) or (II) or a substrate that can be reduced to obtain the same.

专利号:US-7193086-B2
优先权日:2001-05-30
标题:Process for preparation of a quinolinecarbaldehyde
发明人:MATSUMOTO HIROO; SHIMIZU TAKANORI
权利人:DAICEL CHEM
摘要:A process for producing 2-cyclopropyl-4-(4-fluorophenyl)-quinoline-3-carbaldehyde important as intermediate for the synthesis of pharmaceuticals, efficiently from an unnecessary antipode, is provided. n A process for producing 2-cyclopropyl-4-(4-fluorophenyl)-quinoline-3-carbaldehyde represented by the formula (III): n nwhich comprises treating a compound represented by the formula (I) or (II):n n n(wherein A is —CHOH or —C(O)—, and R is a hydrogen atom, a C 1-4 alkyl group which may be branched, a phenyl group, an alkali metal ion or an alkaline earth metal ion) with ozone, followed by reduction with an inorganic sulfur compound or by hydrogenation for reduction decomposition.

专利号:US-2005085555-A1
优先权日:1997-08-21
标 题:Composition, synthesis and therapeutic applications of polyamines
发明人:MURPHY MICHAEL A; MALACHOWSKI MITCHELL R
摘要:This invention relates to a process of synthesis and composition of open chain (ring), closed ring, linear branched and or substituted polyamines, polyamine derived tyrosine phosphatase inhibitors and PPAR partial agonists/partial antagonists via a series of substitution reactions and optimizing the bioavailability and biological activities of the compounds. Polyamines prevent the toxicty of neutoxins and diabetogenic toxins including paraquat, methyphenyl pyridine radical, rotenone, diazoxide, streptozotocin and alloxan. These polyamines can be to treat neurological, cardiovascular, endocrine acquired and inherited mitochondrial DNA damage diseases and other disorders in mammalian subjects, and more specifically to the therapy of Parkinson's disease, Alzheimer's disease, Lou Gehrig's disease, Binswanger's disease, Olivopontine Cerebellar Degeneration, Lewy Body disease, Diabetes, Stroke, Atherosclerosis, Myocardial Ischemia, Cardiomyopathy, Nephropathy, Ischemia, Glaucoma, Presbycussis, Cancer, Osteoporosis, Rheumatoid Arthritis, Inflammatory Bowel Disease, Multiple Sclerosis and as Antidotes to Toxin Exposure.
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主要参考文献

[参考文献]: Chandrasekaran Rajarajeswari, Et Al. Mixed Ligand Copper(Ii) Complexes Of 1,10-Phenanthroline With Tridentate Phenolate/pyridyl/(Benz)Imidazolyl Schiff Base Ligands: Covalent Vs Non-Covalent Dna Binding, Dna Cleavage And Cytotoxicity. J Inorg Biochem. 2014 Nov:140:255-68.
[参考文献]: Tamara Rodríguez-Cabo, Et Al. Time-Of-Flight Accurate Mass Spectrometry Identification Of Quinoline Alkaloids In Honey. Anal Bioanal Chem. 2015 Aug;407(20):6159-70.

合成参考文献


参考文献:10.1107/s1600536811012955
摘要:Djamel D, Tahar D, Djahida H, Hanane H, Salah C. 4,4′-Oxybis{N-[(E)-quinolin-2-ylmethylidene]aniline}. Acta Crystallogr E Struct Rep Online. 2011 Apr 13;67(5):o1119–20. doi: 10.1107/s1600536811012955.
参考文献:10.1107/s1600536811016011
摘要:Djamel D, Tahar D, Djahida H, Hanane H, Salah C. 4,4′-Methylenebis{N-[(E)-quinolin-2-ylmethylidene]aniline}. Acta Crystallogr E Struct Rep Online. 2011 May 07;67(6):o1318. doi: 10.1107/s1600536811016011.
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