2-methoxy-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-10-carboxaldehyde | 384331-29-7

• 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: 2-methoxy-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-10-carboxaldehyde
• 英文别名: 2-methoxy-6,7,8,9-tetrahydropyrido[1,2-a]indole-10-carbaldehyde
• CAS: 384331-29-7
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: YTPWKQQLWHFMMP-UHFFFAOYSA-N

物化性质

• 沸点：
  439.5±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methoxy-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-10-carboxaldehyde 在 lithium aluminium tetrahydride 、 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 生成 2-(2-methoxy-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)ethanamine
  参考文献：
  名称：

  Synthesis of new tricyclic melatoninergic ligands

  摘要：

  We report the synthesis and biological evaluation of a series of new tricyclic analogs of the hormone melatonin, which act as probes of the constraints at the hormone's receptor site with regard to the lower N1-C2 region of the indole moiety of melatonin. Three of the new compounds, N-[2-(2-methoxy-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)ethyl]acetamide (9), and the respective propionamide 10 and butyramide 11, are as potent as melatonin in the Xenopus laevis melanophore model. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01125-9
• 作为产物：
  描述：

  5-methoxy-2-[(4-methylphenyl)sulfonyl]-1H-indole 在 氢氧化钾 、 偶氮二异丁腈 、 三正丁基氢锡 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.5h， 生成 2-methoxy-6,7,8,9-tetrahydro-pyrido[1,2-a]indole-10-carboxaldehyde
  参考文献：
  名称：

  Synthesis of new tricyclic melatoninergic ligands

  摘要：

  We report the synthesis and biological evaluation of a series of new tricyclic analogs of the hormone melatonin, which act as probes of the constraints at the hormone's receptor site with regard to the lower N1-C2 region of the indole moiety of melatonin. Three of the new compounds, N-[2-(2-methoxy-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)ethyl]acetamide (9), and the respective propionamide 10 and butyramide 11, are as potent as melatonin in the Xenopus laevis melanophore model. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01125-9

文献信息

• Pyrroloindoles, pyridoindoles and azepinoindoles as 5-ht2c agonists
  申请人：Vernalis Research Limited

  公开号：US06433175B1

  公开（公告）日：2002-08-13

  A chemical compound of formula (I), wherein n is 1, 2 or 3; R1 and R2 are independently selected from hydrogen and alkyl; R3 is alkyl; R4 to R7 are independently selected from hydrogen, halogen, hydroxy, alkyl, aryl, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfoxyl, alkylsulfonyl, arylsulfoxyl, arylsulfonyl, amino, monoalkylamino, dialkylamino, nitro, cyano, carboxaldehyde, alkylcarbonyl, arylcarbonyl, aminocarbonyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonylamino, aminocarbonyloxy, monoalkylaminocarbonyloxy, dialkylaminocarbonyloxy, monoalkylaminocarbonylamino and dialkylaminocarbonylamino, or R5 and R6 together form a carbocyclic or heterocyclic ring, and pharmaceutically acceptable salts and prodrugs thereof, and the use thereof in therapy, particularly for the treatment of disorders of the central nervous system; damage to the central nervous system; cardiovascular disorders; gastrointestinal disorders, diabetes insipidus, and sleep apnea, and particularly for the treatment of obesity

  化学式（I）的化合物，其中n为1、2或3；R1和R2独立选择自氢和烷基；R3为烷基；R4至R7独立选择自氢、卤素、羟基、烷基、芳基、烷氧基、芳氧基、烷基硫基、芳基硫基、烷基亚氧基、烷基磺醚基、芳基亚氧基、芳基磺醚基、氨基、单烷基氨基、双烷基氨基、硝基、氰基、羰基、烷基羰基、芳基羰基、氨基羰基、单烷基氨基羰基、双烷基氨基羰基、烷氧羰基氨基、氨基羰氧基、单烷基氨基羰氧基、双烷基氨基羰氧基、单烷基氨基羰基氨基和双烷基氨基羰基氨基，或R5和R6一起形成碳环或杂环，以及其药学上可接受的盐和前药，以及其在治疗中的使用，特别是用于治疗中枢神经系统紊乱；中枢神经系统损伤；心血管疾病；胃肠道疾病、尿崩症和睡眠呼吸暂停症，特别是用于肥胖症的治疗。
• Synthesis and biological evaluation of new β,β′-disubstituted 6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl ethylamido melatoninergic ligands
  作者：A Tsotinis、M Panoussopoulou、K Hough、D Sugden

  DOI：10.1016/s0928-0987(03)00020-4

  日期：2003.4

  Tricyclic analogs of melatonin with alkyl and cycloalkyl moieties in the beta position of the ethylamido chain have been prepared and tested for their ability to activate pigment granule aggregation in Xenopus laevis melanophores. The introduction of two methyl groups in the beta position of the side-chain of the methoxyl-substituted ligands induces a synergistic effect in agonist potency, which, importantly, is maintained after the methoxyl substituent is removed. The presence of more bulky beta-substituents, regardless of the size of the R group, seems to lead to antagonism. (C) 2003 Elsevier Science B.V. All rights reserved.
• PYRROLOINDOLES, PYRIDOINDOLES AND AZEPINOINDOLES AS 5-HT2C AGONISTS
  申请人：VERNALIS RESEARCH LIMITED

  公开号：EP1109813B1

  公开（公告）日：2004-08-11
• US6433175B1
  申请人：——

  公开号：US6433175B1

  公开（公告）日：2002-08-13
• Synthesis of new tricyclic melatoninergic ligands
  作者：Andrew Tsotinis、Maria Panoussopoulou、Sachi Sivananthan、David Sugden

  DOI：10.1016/s0014-827x(01)01125-9

  日期：2001.8

  We report the synthesis and biological evaluation of a series of new tricyclic analogs of the hormone melatonin, which act as probes of the constraints at the hormone's receptor site with regard to the lower N1-C2 region of the indole moiety of melatonin. Three of the new compounds, N-[2-(2-methoxy-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)ethyl]acetamide (9), and the respective propionamide 10 and butyramide 11, are as potent as melatonin in the Xenopus laevis melanophore model. (C) 2001 Elsevier Science S.A. All rights reserved.