7-hydroxy-6,7,8,9-tetrahydropyrido[1,2-a]indole | 131849-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 7-hydroxy-6,7,8,9-tetrahydropyrido[1,2-a]indole
• 英文别名: 6,7,8,9-tetrahydropyrido[1,2-a]indol-7-ol；6,7,8,9-tetrahydro-7-hydroxypyrido[1,2-a]indole
• CAS: 131849-30-4
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: PIIAZQCONRBYOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  7-hydroxy-6,7,8,9-tetrahydropyrido[1,2-a]indole 在 4-二甲氨基吡啶 、 sodium azide 、 palladium on carbon 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.5h， 生成 (+/-) 4-fluoro-N-methyl-N-(6,7,8,9-tetrahydropyrido[1,2-a]indol-7-yl)benzenesulfonamide
  参考文献：
  名称：

  New indole amide derivatives as potent CRTH2 receptor antagonists

  摘要：

  A new series of indole amide acting as hCRTH2 receptor ligands had been explored and are described herein. Several amide derivatives displaying low nanomolar activity in hCRTH2 binding and whole blood assays were identified. They were found to behave as a full antagonists, exhibiting good selectivity over related prostaglandin receptors. Also, prototypical compounds in this novel series which displayed acceptable CYP profiles and were orally bioavailable in rats were identified. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.085
• 作为产物：
  描述：

  1-allyl-1H-indole-2-carbaldehyde 在 palladium dihydroxide aluminum oxide 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 96.0h， 生成 7-hydroxy-6,7,8,9-tetrahydropyrido[1,2-a]indole
  参考文献：
  名称：

  分子内硝酮环加成反应可得到吡咯并-和吡啶并[1,2-a]吲哚衍生物。空间因素对区域选择性产物形成的影响。

  摘要：

  从N-烯丙基取代的2-吲哚甲醛开始，并利用分子内硝酮环加成法，我们合成了许多外消旋和对映体纯形式的标题稠环吲哚衍生物。

  DOI：

  10.1021/jo000842g

文献信息

• 4-\x9b3-indolyl!-1H-pyrrolone
  申请人：Hoffmann-La Roche Inc.

  公开号：US05721245A1

  公开（公告）日：1998-02-24

  A compound of the formula ##STR1## wherein R is hydrogen or hydroxy, R.sup.1 and R.sup.2 taken together are a group of the formula --(CH.sub.2).sub.m -- and R.sup.7 is hydrogen or R.sup.1 and R.sup.7 taken together are a group of the formula --(CH.sub.2).sub.n -- and R.sup.2 is hydrogen; R.sup.3 is an aryl or aromatic heterocyclic group; R.sup.4, R.sup.5 and R.sup.6 each independently are hydrogen, halogen, alkyl, hydroxy, alkoxy, haloalkyl, nitro, amino, acylamino, alkylthio, alkylsulfinyl or alkylsulfonyl; R.sup.8 is a group of the formula --(CH.sub.2).sub.p --R.sup.9 or --(CH.sub.2).sub.q --R.sup.10 ; R.sup.9 is hydrogen, alkylcarbonyl, aminoalkylcarbonyl, cyano, amidino, alkoxycarbonyl, aryloxycarbonyl, alkylsulfonyl, aminocarbonyl or aminothiocarbonyl; R.sup.10 is hydroxy, alkoxy, halogen, amino, monoalkylamino, dialkylamino, trialkylamino, azido, acylamino, alkylsulfonylamino, a 5- or 6-membered saturated nitrogen-containing heterocycle; X and Y are oxygen; Z is CH; m, p and q are, independently, an integer from 0 to 5, and n an integer from 1 to 5, as well as pharmaceutically acceptable salts thereof which are useful in the control of inflammatory, immunological, oncological, bronchopulmonary or cardiovascular disorders.

  公式的化合物，其中R是氢或羟基，R1和R2共同构成组--(CH2)m--，R7是氢或R1和R7共同构成组--(CH2)n--，且R2是氢；R3是一种芳香族或芳香杂环群；R4、R5和R6各自独立地为氢、卤素、烷基、羟基、烷氧基、卤代烷基、硝基、氨基、酰氨基、烷基硫醚、烷基亚磺酰基或烷基磺酰基；R8是组--(CH2)p--R9或--(CH2)q--R10；R9是氢、烷基碳酰基、氨基烷基碳酰基、氰基、脒基、烷氧基碳酰基、芳氧基碳酰基、烷基磺酰基、氨基甲酰基或硫代氨基甲酰基；R10是羟基、烷氧基、卤素、氨基、一烷基胺、二烷基胺、三烷基胺、叠氮基、酰氨基、烷基磺酰氨基、一个5或6成员的饱和含氮杂环；X和Y是氧；Z是CH；m、p和q各自独立地为0到5的整数，n为1到5的整数，以及作为药物可接受的盐，其在控制炎症、免疫、肿瘤、支气管肺或心血管疾病方面是有用的。
• [EN] INDOLE DERIVATIVES AS CRTH2 RECEPTOR ANTAGONISTS<br/>[FR] DÉRIVÉS D'INDOLE UTILISABLES EN TANT QU'ANTAGONISTES DU RÉCEPTEUR CRTH2
  申请人：MERCK FROSST CANADA LTD

  公开号：WO2010031182A1

  公开（公告）日：2010-03-25

  The compound (+) 7R-[[(4-fluorophenyl)sulfonyl](methyl)ammo]-6,7,8,9-tetrahydropyrido[1,2-a]mdol-10-yl}acetic acid and pharmaceutically acceptable salts thereof are antagonists of the PGD2 receptor, CRTH2, and as such are useful in the treatment and/or prevention of CRTH2-meidated diseases such as asthma.

  (+)7R-[[(4-氟苯基)磺酰](甲基)氨基]-6,7,8,9-四氢吡啶并[1,2-a]吲哚-10-基}乙酸及其药用盐是PGD2受体CRTH2的拮抗剂，因此在治疗和/或预防CRTH2介导的疾病如哮喘中是有用的。
• [EN] HETEROARYL COMPOUNDS FOR KINASE INHIBITION<br/>[FR] COMPOSÉS HÉTÉROARYLE D'INHIBITION DE LA KINASE
  申请人：ARIAD PHARMA INC

  公开号：WO2016183278A1

  公开（公告）日：2016-11-17

  Compounds and pharmaceutical compositions that modulate kinase activity, including mutant EGFR and mutant HER2 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including mutant EGFRand mutant HER2 activity, are described herein.

  本文描述了调节激酶活性的化合物和药物组合物，包括突变EGFR和突变HER2激酶活性，以及与激酶活性相关的疾病和病况的治疗方法、化合物和药物组合物，包括突变EGFR和突变HER2活性。
• Indole derivatives as crth2 receptor antagonists
  申请人：Wang Zhaoyin

  公开号：US20090286825A1

  公开（公告）日：2009-11-19

  Compounds according to formula (I) wherein the radicals R 1 , R 2 and R 3 are as herein defined, and wherein Ar represents an aryl group or heteroaryl group, preferably phenyl, n is 1 or 2, and the radical X represents a group selected from —C(R a )(R b )—, —C(R a )(R b )—C(R a )(R b )—, —C(R a )═C(R a )—, OC(R a )(R b )— or SC(R a )(R b )—. These compounds and their pharmaceutical acceptable salts are used in pharmaceutical compositions as prostaglandine D2 receptor antagonists useful in the treatment of CRTH2-mediated diseases such as respiratory, inflammatory or allergic conditions among others.

  化合物的公式为（I），其中基团R1、R2和R3如所定义，Ar代表芳基或杂芳基，优选苯基，n为1或2，基团X代表从—C（Ra）（Rb）—，—C（Ra）（Rb）—C（Ra）（Rb）—，—C（Ra）═C（Ra）—，OC（Ra）（Rb）—或SC（Ra）（Rb）—中选择的基团。这些化合物及其药学上可接受的盐用于制备药物组合物，作为前列腺素D2受体拮抗剂，对治疗CRTH2介导的疾病，如呼吸系统、炎症或过敏等病症有用。
• INDOLE DERIVATIVES AS CRTH2 RECEPTOR ANTAGONISTS
  申请人：Wang Zhaoyin

  公开号：US20110201641A1

  公开（公告）日：2011-08-18

  The compound (+) 7R-[[(4-fluorophenyl)sulfonyl] (methyl)ammo]-6,7,8,9-tetrahydropyrido[1,2-a]mdol-10-yl}acetic acid and pharmaceutically acceptable salts thereof are antagonists of the PGD2 receptor, CRTH2, and as such are useful in the treatment and/or prevention of CRTH2-meidated diseases such as asthma.

  复合物（+）7R-[[(4-氟苯基)磺酰基]（甲基）氨基]-6,7,8,9-四氢吡啶[1,2-a]咪唑-10-基}乙酸及其药学上可接受的盐是PGD2受体，CRTH2的拮抗剂，因此在治疗和/或预防CRTH2介导的疾病，如哮喘中有用。