5-chloro-imidazo[1,2-a]quinoline-2-carboxylic acid ethyl ester | 67817-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-chloro-imidazo[1,2-a]quinoline-2-carboxylic acid ethyl ester
• 英文别名: ethyl 5-chloroimidazo-[1,2-a]-quinoline-2-carboxylate；Ethyl 5-chloroimidazo[1,2-a]quinoline-2-carboxylate
• CAS: 67817-46-3
• 化学式: C₁₄H₁₁ClN₂O₂
• 分子量: 274.707
• InChiKey: SORCAEJRFCXLDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-imidazo[1,2-a]quinoline-2-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以66%的产率得到5-chloro-imidazo[1,2-a]quinoline-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles

  摘要：

  4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.

  DOI：

  10.1021/jm00401a009
• 作为产物：
  描述：

  2-氨基-4-氯喹啉 、 3-溴丙酮酸乙酯 在 乙醚 、 乙醇 、 氯仿 、 disodium;carbonate 、 水 、 甲醇 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.5h， 以to obtain fine white needles of ethyl 5-chloroimidazo-[1,2-a]-quinoline-2-carboxylate melting at 169°-170° C.的产率得到5-chloro-imidazo[1,2-a]quinoline-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Novel imidazoquinolines

  摘要：

  化合物的式子为 ##STR1## 其中X和Y分别选自氢，卤素和1至5个碳原子的烷氧基组成的群，Z选自氢，1至5个碳原子的烷基，可选择性地用至少两个羟基或保护羟基取代，以及 ##STR2## n为1至6的整数，R.sub.1和R.sub.2分别为1至5个碳原子的烷基，并与它们连接的氮一起形成含有4至6个碳原子的饱和杂环环，并可由另一个杂原子中断，该另一个杂原子可选择性地用1至5个碳原子的烷基取代，以及具有抗过敏和支气管扩张活性的非毒性、药学上可接受的盐及其制备方法。

  公开号：

  US04279912A1

文献信息

• Novel imidazoquinolines
  申请人：Roussel Uclaf

  公开号：US04279912A1

  公开（公告）日：1981-07-21

  Novel imidazoquinolines of the formula ##STR1## wherein X and Y are individually selected from the group consisting of hydrogen, halogen and alkoxy of 1 to 5 carbon atoms, Z is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms optionally substituted with at least two hydroxyls or protected hydroxyls and ##STR2## n is an integer from 1 to 6 and R.sub.1 and R.sub.2 are individually alkyl of 1 to 5 carbon atoms and taken together with the nitrogen to which they are attached form a saturated heterocyclic ring containing 4 to 6 carbon atoms and optionally interrupted by another heteroatom which further heteroatom is optionally substituted with alkyl of 1 to 5 carbon atoms and non-toxic, pharmaceutically acceptable salts thereof having antiallergic and bronchodilatory activity and their preparations.

  新型咪唑喹啉的化学式为##STR1##其中X和Y分别选自氢、卤素和1至5个碳原子的烷氧基组成的群，Z选自氢、1至5个碳原子的烷基，可选地被至少两个羟基或保护羟基取代，并且##STR2##n是1至6的整数，R.sub.1和R.sub.2分别是1至5个碳原子的烷基，并与它们连接的氮一起形成含有4至6个碳原子的饱和杂环环，可选地被另一个杂原子中断，该另一个杂原子可选地被1至5个碳原子的烷基取代，以及其无毒、药学上可接受的盐，具有抗过敏和支气管扩张活性以及它们的制备。
• Anti-allergenic 5-alkoxyimidazo[1,2-A]quinoline-2-carboxylic acids and
  申请人：Pfizer Inc.

  公开号：US04075343A1

  公开（公告）日：1978-02-21

  A novel series of 5-alkoxyimidazo[1,2-a]quinoline-2-carboxylic acids and esters thereof of the formula (I) ##STR1## wherein R is hydrogen or alkyl having from one to five carbon atoms; each of R.sup.1 and R.sup.2 is hydrogen, alkyl having from one to five carbon atoms, alkoxy having from one to five carbon atoms, fluoro, chloro, bromo, methylthio or methylsulfinyl, with the proviso that when R.sup.1 and R.sup.2 are both bulky groups, i.e. branched chain alkyl or branched chain alkoxy, they are located on non-adjacent positions; and when R.sup.1 and R.sup.2 are taken together they form tetramethylene, 1,3-butadienyl, methylenedioxy or ethylenedioxy, each said group being attached to adjacent carbon atoms of the benzenoid ring; R.sup.3 is alkyl having from one to five carbon atoms; and the pharmaceutically acceptable cationic salts of those compounds wherein R is hydrogen; compositions thereof; their use as antiallergy agents and certain intermediates for the preparation of said compounds of formula (I).

  一系列的5-烷氧基咪唑并[1,2-a]喹啉-2-羧酸及其酯类，其化学式为(I) ##STR1## 其中，R为氢或具有1-5个碳原子的烷基；R.sup.1和R.sup.2中的每个都是氢、具有1-5个碳原子的烷基、具有1-5个碳原子的烷氧基、氟、氯、溴、甲硫基或甲基磺酰基，但是当R.sup.1和R.sup.2均为臃肿基，即支链烷基或支链烷氧基时，它们位于非相邻的位置；当R.sup.1和R.sup.2结合在一起时，它们形成四亚甲基、1,3-丁二烯基、亚甲基二氧基或乙基二氧基，每个所述基固定于苯环上相邻的碳原子上；R.sup.3为具有1-5个碳原子的烷基；以及其中R为氢的药学上可接受的阳离子盐；它们的组成物；它们作为抗过敏剂的用途以及制备上述化合物(I)的某些中间体。
• AGER, IAN R.;BARNES, ALAN C.;DANSWAN, GEOFFREY W.;HAIRSINE, PETER W.;KAY,+, J. MED. CHEM., 31,(1988) N 6, 1098-1115
  作者：AGER, IAN R.、BARNES, ALAN C.、DANSWAN, GEOFFREY W.、HAIRSINE, PETER W.、KAY,+

  DOI：——

  日期：——
• US4075343A
  申请人：——

  公开号：US4075343A

  公开（公告）日：1978-02-21
• US4279912A
  申请人：——

  公开号：US4279912A

  公开（公告）日：1981-07-21