2-(4-氯苯基)咪唑并[1,2-a]吡啶-3-乙酸 | 17745-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(4-氯苯基)咪唑并[1,2-a]吡啶-3-乙酸
• 英文名称: [2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl]acetic acid
• 英文别名: [2-(4-chloro-phenyl)-imidazo[1,2-a]pyridin-3-yl]-acetic acid；3-Carboxymethyl-2-(4-chlor-phenyl)-imidazo<1.2-a>pyridin；Imidazo(1,2-a)pyridine-3-acetic acid, 2-(p-chlorophenyl)-；2-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl]acetic acid
• CAS: 17745-06-1
• 化学式: C₁₅H₁₁ClN₂O₂
• 分子量: 286.718
• InChiKey: ZPHLXYYPDRCBMG-UHFFFAOYSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二甲胺 、 2-(4-氯苯基)咪唑并[1,2-a]吡啶-3-乙酸 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-(2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-N,N-dimethylacetamide
  参考文献：
  名称：

  Lange; Karolak-Wojciechowska; Wejroch, Acta poloniae pharmaceutica, 2001, vol. 58, # 1, p. 43 - 52

  摘要：

  DOI：
• 作为产物：
  描述：

  2-[8-(4-氯苯基)-1,7-二氮杂双环[4.3.0]壬-2,4,6,8-四烯-9-基]乙酰胺 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以82%的产率得到2-(4-氯苯基)咪唑并[1,2-a]吡啶-3-乙酸
  参考文献：
  名称：

  Lange; Karolak-Wojciechowska; Wejroch, Acta poloniae pharmaceutica, 2001, vol. 58, # 1, p. 43 - 52

  摘要：

  DOI：

文献信息

• Processes for the preparation of imidazo[1,2-a] pyridine derivatives
  申请人：Sridharan Ramasubramanian

  公开号：US20060084806A1

  公开（公告）日：2006-04-20

  A process for the preparation of imidazo[1,2-a]pyridine derivatives of the formula I: wherein R is hydrogen, halogen or a C 1 -C 4 alkyl group; R 1 and R 2 are independently hydrogen, a straight or branched C 1 -C 6 alkyl group which is unsubstituted or substituted by one or more halogen atoms, hydroxyl, N(C 1 -C 4 alkyl) 2 , carbamoyl or C 1 -C 4 alkoxy radicals, a C 1 -C 6 alkyl hydroxy group, a C 3 -C 6 cycloalkyl radical, a benzyl radical, a phenyl radical or R 1 and R 2 together with the nitrogen atom to which they are bonded are joined together to form a substituted or unsubstituted heterocyclic group optionally containing one or more additional heterocyclic atoms; and R 3 and R 4 are independently hydrogen, halogen or a C 1 -C 4 alkyl group, or a pharmaceutically acceptable salt thereof, the process comprising (a) reacting an imidazo[1,2-a]pyridine carboxylic acid of the formula II wherein R, R 3 and R 4 have the aforestated meanings with a halogenating agent in the absence of a solvent to form an acid halide intermediate and (b) reacting the acid halide intermediate with an amine of the formula HNR 1 R 2 wherein R 1 and R 2 have the aforestated meanings to form the compound of formula I.

  一种制备式I的咪唑[1,2-a]吡啶衍生物的过程：其中R为氢、卤素或C1-C4烷基；R1和R2独立为氢、直链或支链的未取代或取代一个或多个卤素原子、羟基、N(C1-C4烷基)2、氨基甲酰基或C1-C4烷氧基基团的C1-C6烷基基团、C1-C6烷基羟基、C3-C6环烷基基团、苄基基团、苯基基团或R1和R2连同它们连接的氮原子一起形成一个取代或未取代的杂环基团，该基团可选地含有一个或多个额外的杂环原子；R3和R4独立为氢、卤素或C1-C4烷基，或其药学上可接受的盐，该过程包括（a）在无溶剂的情况下将式II的咪唑[1,2-a]吡啶羧酸（其中R，R3和R4具有上述含义）与卤代试剂反应以形成酸卤中间体，和（b）将酸卤中间体与式HNR1R2的胺（其中R1和R2具有上述含义）反应以形成式I的化合物。
• Synthesis of Substituted Imidazo[1,2-a]Pyridin-3-yl-Acetic Acids by Multicomponent Condensation of 2-Aminopyridines with Arylglyoxals and Meldrum’s Acid
  作者：Boris V. Lichitsky、Аleksander D. Tretyakov、Andrey N. Komogortsev、Vitaly S. Mityanov、Arkady А. Dudinov、Mikhail M. Krayushkin

  DOI：10.1007/s10593-019-02432-6

  日期：2019.2

  A simple and effective method for the synthesis of substituted imidazo[1,2-a]pyridin-3-yl-acetic acids has been developed based on the multicomponent condensation of 2-aminopyridines with arylglyoxals and Meldrum's acid.

  基于2-氨基吡啶与芳基乙二醛和Meldrum酸的多组分缩合，已经开发了一种简单有效的合成取代的咪唑并[1,2 - a ]吡啶-3-基乙酸的方法。
• Imidazo[1,2-a] pyridine derivatives and their application as
  申请人：Synthelabo

  公开号：US04382938A1

  公开（公告）日：1983-05-10

  Imidazo[1,2-a] pyridines of the formula: ##STR1## and their acid addition salts in which Y represents a hydrogen or halogen atom or a C.sub.1-4 alkyl radical, Z represents a naphthyl radical or a radical ##STR2## in which each of X.sub.1 and X.sub.2 independently of one another is a hydrogen or halogen atom, a C.sub.1-4 alkoxy radical, a C.sub.1-6 alkyl radical or CF.sub.3, CH.sub.3 S--, CH.sub.3 SO.sub.2 --, --NO.sub.2, --NH.sub.2 or --NHCOCH.sub.3, and each of R.sub.1 and R.sub.2 independently of one another represents a hydrogen atom, a straight or branched C.sub.1-5 alkyl radical which is unsubstituted or substituted by one or more halogen atoms or hydroxyl, --N(C.sub.1-4 alkyl).sub.2, carbamoyl or C.sub.1-4 alkoxy radicals, allyl, propargyl, a C.sub.3-6 cycloalkyl radical, benzyl, or phenyl, not both R.sub.1 and R.sub.2 being hydrogen, or --NR.sub.1 R.sub.2 represents a heterocyclic ring containing from 3 to 6 carbon atoms, or a heterocyclic ring of the formula ##STR3## in which X is O, S, CHOR' or >N--R, R' being hydrogen or benzyl and R being hydrogen, a C.sub.1-4 alkyl radical, or phenyl which is unsubstituted or substituted by methoxy or a halogen atom, which may be made from the corresponding acids, have valuable pharmacological properties, especially anxiolytic, anti-anoxic, sleep-inducing, hypnotic and anticonvulsant properties.

  公式：##STR1##中的咪唑[1,2-a]吡啶及其酸加合物，其中Y代表氢或卤素原子或C.sub.1-4烷基基团，Z代表萘基团或基团##STR2##其中X.sub.1和X.sub.2各自独立地是氢或卤素原子，C.sub.1-4烷氧基，C.sub.1-6烷基或CF.sub.3，CH.sub.3S--，CH.sub.3SO.sub.2--，--NO.sub.2，--NH.sub.2或--NHCOCH.sub.3，而R.sub.1和R.sub.2各自独立地代表氢原子，直链或支链C.sub.1-5烷基，未取代或取代一个或多个卤素原子或羟基，--N(C.sub.1-4烷基).sub.2，氨基甲酰基或C.sub.1-4烷氧基基团，烯丙基，丙炔基，C.sub.3-6环烷基，苄基或苯基，R.sub.1和R.sub.2不都是氢，或--NR.sub.1R.sub.2代表含有3至6个碳原子的杂环或式的杂环##STR3##其中X为O，S，CHOR'或>N--R，R'为氢或苄基，R为氢，C.sub.1-4烷基基团或苯基，未取代或取代甲氧基或卤素原子，这些化合物具有有价值的药理学特性，特别是抗焦虑、抗缺氧、催眠、催眠和抗惊厥特性。
• 6-Methyl-2-(4-methylthiophenyl)-i
  申请人：Synthelabo

  公开号：US04460592A1

  公开（公告）日：1984-07-17

  6-Methyl-2-(4-methylthiophenyl)-imidazo[1,2-a]-pyridine-3-N,N-dimethylaceta mide is provided, preferably in the form of a pharmaceutically acceptable salt, for example, 6-methyl-2-(4-methylthiophenyl)-imidazo[1,2-a]-pyridine-3-N,N-dimethylacet amide methylsulfate. Also provided is a method of providing a patient with a hypnotic effect which comprises administering to said patient a hynotically effective amount of the compound 6-methyl-2-(4-methylthiophenyl)-imidazo[1,2-a]-pyridine-3-N,N-dimethylacet amide or a pharmaceutically acceptable salt thereof.

  提供了6-甲基-2-(4-甲基硫代苯基)-咪唑[1,2-a]-吡啶-3-N,N-二甲基乙酰胺，最好以药学上可接受的盐的形式提供，例如6-甲基-2-(4-甲基硫代苯基)-咪唑[1,2-a]-吡啶-3-N,N-二甲基乙酰胺甲硫酸盐。还提供了一种提供催眠效果给患者的方法，包括向该患者给予有效催眠剂量的化合物6-甲基-2-(4-甲基硫代苯基)-咪唑[1,2-a]-吡啶-3-N,N-二甲基乙酰胺或其药学上可接受的盐。
• KAPLAN, J. -P.;GEORGE, P.
  作者：KAPLAN, J. -P.、GEORGE, P.

  DOI：——

  日期：——