5-methoxy-1-n-propylindole-3-carboxaldehyde | 128600-67-9

• 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: 5-methoxy-1-n-propylindole-3-carboxaldehyde
• 英文别名: 5-Methoxy-1-propyl-1H-indole-3-carbaldehyde；5-methoxy-1-propylindole-3-carbaldehyde
• CAS: 128600-67-9
• 化学式: C₁₃H₁₅NO₂
• mdl: MFCD07186534
• 分子量: 217.268
• InChiKey: KNBADAAZAKZNQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  5-methoxy-1-n-propylindole-3-carboxaldehyde 在 lithium aluminium tetrahydride 、 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 30.75h， 生成 (+/-)-1-(5-methoxy-n-propylindol-3-yl)-2-aminopropane
  参考文献：
  名称：

  Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region

  摘要：

  Taking advantage of a proposed hydrophobic region on 5-HT2 receptors previously identified by radioligand-binding studies utilizing various phenylisopropylamine derivatives, we prepared and evaluated several N1 - and/or C7-alkyl-substituted derivatives of alpha-methyltryptamine in order to improve its affinity and selectivity. It was determined that substitution of an n-propyl or amyl group has similar effect on affinity regardless of location (i.e., N1 or C7). The low affinity of several N1-alkylpyrroleethylamines suggests that the benzene portion of the alpha-methyltryptamines is necessary for significant affinity. Whereas tryptamine derivatives generally display little selectivity for the various populations of 5-HT receptors, N1-n-propyl-5-methoxy-alpha-methyltryptamine (3h) binds with significant affinity (Ki = 12 nM) and selectivity at 5-HT2 receptors relative to 5-HT1A (Ki = 7100 nM), 5-HT1B (Ki = 5000 nM), 5-HT1C (Ki = 120 nM), and 5-HT1D (Ki greater than 10,000 nM) receptors. As a consequence, this is the most 5-HT2-selective indolylalkylamine derivative reported to date.

  DOI：

  10.1021/jm00172a016
• 作为产物：
  描述：

  5-甲氧基吲哚 在 sodium hydride 、 三氯氧磷 作用下， 反应 25.5h， 生成 5-methoxy-1-n-propylindole-3-carboxaldehyde
  参考文献：
  名称：

  Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region

  摘要：

  Taking advantage of a proposed hydrophobic region on 5-HT2 receptors previously identified by radioligand-binding studies utilizing various phenylisopropylamine derivatives, we prepared and evaluated several N1 - and/or C7-alkyl-substituted derivatives of alpha-methyltryptamine in order to improve its affinity and selectivity. It was determined that substitution of an n-propyl or amyl group has similar effect on affinity regardless of location (i.e., N1 or C7). The low affinity of several N1-alkylpyrroleethylamines suggests that the benzene portion of the alpha-methyltryptamines is necessary for significant affinity. Whereas tryptamine derivatives generally display little selectivity for the various populations of 5-HT receptors, N1-n-propyl-5-methoxy-alpha-methyltryptamine (3h) binds with significant affinity (Ki = 12 nM) and selectivity at 5-HT2 receptors relative to 5-HT1A (Ki = 7100 nM), 5-HT1B (Ki = 5000 nM), 5-HT1C (Ki = 120 nM), and 5-HT1D (Ki greater than 10,000 nM) receptors. As a consequence, this is the most 5-HT2-selective indolylalkylamine derivative reported to date.

  DOI：

  10.1021/jm00172a016

文献信息

• (5-MEMBERED)-(5-MEMBERED) OR (5-MEMBERED)-(6-MEMBERED) FUSED RING CYCLOALKYLAMINE DERIVATIVE
  申请人：MSD K.K.

  公开号：EP2319841A1

  公开（公告）日：2011-05-11

  Disclosed are a compound of a formula (I) and its pharmaceutically-acceptable salt: wherein Q is CH or N; R1a, R1b, R1c and R1d are independently a C1-6 alkyl, a halo-C1-6 alkyl, etc.; R2 is a hydrogen atom, etc.; R3 is independently a hydrogen atom, a C1-6 alkyl, etc., or two R3'S, taken together, form a bridge such as methylene, etc.; R4 and R4b are independently a hydrogen atom, a C1-6 alkyl, etc.; Z is a bicyclic aromatic hetero ring, etc.; Ar is a benzene ring, etc.; m1 and m2 are independently 0, 1 or 2; n is an integer of from 1 to 4. The compound and its salt act as a melanin concentrating hormone receptor antagonist, and are useful as a preventive or remedy for central system disorders, cardiovascular disorders, metabolic disorders, etc.

  本发明公开了一种具有化学式（I）及其药用可接受盐的化合物：其中Q为CH或N；R1a、R1b、R1c和R1d独立地为C1-6烷基、卤代C1-6烷基等；R2为氢原子等；R3独立地为氢原子、C1-6烷基等，或两个R3'结合在一起形成例如亚甲基等的桥；R4和R4b独立地为氢原子、C1-6烷基等；Z为双环芳香杂环、等；Ar为苯环等；m1和m2独立地为0、1或2；n为1至4的整数。该化合物及其盐作为黑色素浓集激素受体拮抗剂，并且可用作中枢系统紊乱、心血管紊乱、代谢紊乱等的预防或治疗。
• 5/5-OR 5/6-MEMBERED CONDENSED RING CYCLOALKYLAMINE DERIVATIVE
  申请人：Kishino Hiroyuki

  公开号：US20110124674A1

  公开（公告）日：2011-05-26

  Disclosed are a compound of a formula (I) and its pharmaceutically-acceptable salt: wherein Q is CH or N; R 1a , R 1b , R 1c and R 1d are independently a C 1-6 alkyl, a halo-C 1-6 alkyl, etc.; R 2 is a hydrogen atom, etc.; R 3 is independently a hydrogen atom, a C 1-6 alkyl, etc., or two R 3 's, taken together, form a bridge such as methylene, etc.; R 4a and R 4b are independently a hydrogen atom, a C 1-6 alkyl, etc.; Z is a bicyclic aromatic hetero ring, etc.; Ar is a benzene ring, etc.; m1 and m2 are independently 0, 1 or 2; n is an integer of from 1 to 4. The compound and its salt act as a melanin concentrating hormone receptor antagonist, and are useful as a preventive or remedy for central system disorders, cardiovascular disorders, metabolic disorders, etc.

  本发明公开了一种化合物及其药学上可接受的盐，其化学式为（I）： 其中，Q是CH或N；R1a，R1b，R1c和R1d独立地表示C1-6烷基，卤代C1-6烷基等；R2是氢原子等；R3独立地表示氢原子，C1-6烷基等，或者两个R3共同形成例如亚甲基等的桥；R4a和R4b独立地表示氢原子，C1-6烷基等；Z是双环芳香杂环，等；Ar是苯环等；m1和m2独立地表示0、1或2；n是1至4的整数。该化合物及其盐作为黑色素浓集激素受体拮抗剂，可用于预防或治疗中枢系统疾病、心血管疾病、代谢性疾病等。
• GLENNON, RICHARD A.;CHAURASIA, CHANDRA;TITELER, MILT, J. MED. CHEM., 33,(1990) N0, C. 2777-2784
  作者：GLENNON, RICHARD A.、CHAURASIA, CHANDRA、TITELER, MILT

  DOI：——

  日期：——
• [EN] (5-MEMBERED)-(5-MEMBERED) OR (5-MEMBERED)-(6-MEMBERED) FUSED RING CYCLOALKYLAMINE DERIVATIVE<br/>[FR] DÉRIVÉ DE CYCLOALKYLAMINE À NOYAUX FUSIONNÉS À (5 CHAÎNONS)-(5 CHAÎNONS) OU (5 CHAÎNONS)-(6 CHAÎNONS)
  申请人：BANYU PHARMA CO LTD

  公开号：WO2010013595A1

  公开（公告）日：2010-02-04

  【課題】　中枢性疾患、循環器系疾患、代謝性疾患用の医薬品として有用な、メラニン凝集ホルモン受容体の拮抗剤を提供することを目的とする。 【解決手段】　式（Ｉ） 【化１】［式中、Ｑは、ＣＨ又はＮを表し、Ｒ１ａ、Ｒ１ｂ、Ｒ１ｃ及びＲ１ｄは、それぞれ独立して、Ｃ１－６アルキル、ハロＣ１－６アルキル等を表し、Ｒ２は、水素原子等を表し、Ｒ３は、それぞれ独立して、水素原子、Ｃ１－６アルキル等を表すか、２つのＲ３が一緒になって、メチレン等のブリッジを形成し、Ｒ４ａ及びＲ４ｂは、それぞれ独立して、水素原子、Ｃ１－６アルキル等を表し、Ｚは、２環性芳香族複素環等を表し、Ａｒは、ベンゼン環等を表し、ｍ１及びｍ２は、独立して、０、１又は２を表し、ｎは、１～４の整数を表す］で表される化合物又は薬学的に許容されるその塩。
• Binding of indolylalkylamines at 5-HT2 serotonin receptors: examination of a hydrophobic binding region
  作者：Richard A. Glennon、Chandra Chaurasia、Milt Titeler

  DOI：10.1021/jm00172a016

  日期：1990.10

  Taking advantage of a proposed hydrophobic region on 5-HT2 receptors previously identified by radioligand-binding studies utilizing various phenylisopropylamine derivatives, we prepared and evaluated several N1 - and/or C7-alkyl-substituted derivatives of alpha-methyltryptamine in order to improve its affinity and selectivity. It was determined that substitution of an n-propyl or amyl group has similar effect on affinity regardless of location (i.e., N1 or C7). The low affinity of several N1-alkylpyrroleethylamines suggests that the benzene portion of the alpha-methyltryptamines is necessary for significant affinity. Whereas tryptamine derivatives generally display little selectivity for the various populations of 5-HT receptors, N1-n-propyl-5-methoxy-alpha-methyltryptamine (3h) binds with significant affinity (Ki = 12 nM) and selectivity at 5-HT2 receptors relative to 5-HT1A (Ki = 7100 nM), 5-HT1B (Ki = 5000 nM), 5-HT1C (Ki = 120 nM), and 5-HT1D (Ki greater than 10,000 nM) receptors. As a consequence, this is the most 5-HT2-selective indolylalkylamine derivative reported to date.