methyl 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxylate | 203585-25-5

• 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: methyl 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxylate
• 英文别名: oxazino[3,2-a]-indole-10-carboxylate；methyl 3,4-dihydro-2H-[1,3]-oxazino[3,2-a]indole-10-carboxylate
• CAS: 203585-25-5
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: JOPOHNNCBFYVIM-UHFFFAOYSA-N

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：
  0.31
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl 2-(3-chloropropoxy)indole-3-carboxylate	203585-28-8	C13H14ClNO3	267.712

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(1-benzyl-4-piperidinyl)methyl 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxylate	152811-81-9	C25H28N2O3	404.509
  ——	[1-[(4-tert-butylphenyl)methyl]-4-piperidinyl]methyl 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxylate	1444006-50-1	C29H36N2O3	460.616
  ——	2-[4-[[4-(3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carbonyloxymethyl)-1-piperidinyl]methyl]phenyl]-2-methylpropanoic acid	1247008-23-6	C29H34N2O5	490.599
  ——	[1-[[4-(2-methoxy-1,1-dimethyl-2-oxoethyl)phenyl]methyl]-4-piperidinyl]methyl 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxylate	1247008-47-4	C30H36N2O5	504.626
  ——	[1-[[4-[1,1-dimethyl-2-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methoxy]-2-oxoethyl]phenyl]methyl]-4-piperidinyl]methyl 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxylate	1247008-25-8	C34H38N2O8	602.684
  N-[(1-丁基-4-哌啶基)甲基]-3,4-二氢-2H-[1,3]噁嗪并[3,2-a]吲哚-10-羧胺	piboserod	152811-62-6	C22H31N3O2	369.507
  2H-[1,3]氧杂联氮基[3,2-a]吲哚-10-甲酰胺,3,4-二氢-N-[[1-(苯基甲基)-4-哌啶基]甲基]-	3,4-dihydro-N-[1-(phenylmethoxy)-4-piperidinylmethyl]-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide	152811-86-4	C25H29N3O2	403.524
  ——	3,4-dihydro-N-[[1-(3-hydroxybutyl)-4-piperidinyl]methyl]-2H-[1,3]oxazino[3,2-α]indole-10-carboxamide	——	C22H31N3O3	385.506
  ——	N-[[1-[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]butyl]-4-piperidinyl]methyl]-3,4-dihydro-2H-[1,3]oxazino[3,2-α]indole-10-carboxamide	261787-97-7	C28H45N3O3Si	499.769

反应信息

• 作为反应物：
  描述：

  methyl 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxylate 在 palladium on activated charcoal 氢气 、 三甲基铝 、 草酸 作用下， 以 乙醇 、 溶剂黄146 、 甲苯 为溶剂， 45.0 ℃ 、344.74 kPa 条件下， 反应 35.0h， 生成 3,4-dihydro-N-[[1-(3-hydroxybutyl)-4-piperidinyl]methyl]-2H-[1,3]oxazino[3,2-α]indole-10-carboxamide
  参考文献：
  名称：

  Synthesis and pharmacological activity of metabolites of the 5-HT4 receptor antagonist SB-207266

  摘要：

  Three metabolites of N-[(1-butyl-4-piperidinyl)methyl]-3,4-dihydro-2H-[1,3]-oxazino[3,2_a]indole-10-carboxamide (SB-207266) (1) were synthesised and their pharmacological activity determined. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00120-1
• 作为产物：
  描述：

  吲哚-3-甲酸甲酯 在 三乙烯二胺 、 sodium hydroxide 、 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.67h， 生成 methyl 3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole-10-carboxylate
  参考文献：
  名称：

  Synthesis and pharmacological activity of metabolites of the 5-HT4 receptor antagonist SB-207266

  摘要：

  Three metabolites of N-[(1-butyl-4-piperidinyl)methyl]-3,4-dihydro-2H-[1,3]-oxazino[3,2_a]indole-10-carboxamide (SB-207266) (1) were synthesised and their pharmacological activity determined. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00120-1

文献信息

• Process for the preparation of N-[(1-.sup.n
  申请人：Smithkline Beecham plc

  公开号：US06100397A1

  公开（公告）日：2000-08-08

  A process for the preparation of SB 207266 or a pharmaceutically acceptable salt thereof, which process comprises the reaction of N-(1-.sup.n butyl-4-piperidyl)methylamine with a compound of formula (A), ##STR1## wherein R is alkyl.

  一种制备SB 207266或其药学上可接受的盐的方法，该方法包括将N-(1-正丁基-4-哌啶基)甲基胺与式(A)的化合物反应，其中R为烷基。 ##STR1##
• 3,4-Dihdro-N-[[1-(3-hydroxybutyl)-4-piperidinyl]methyl]-2H-[1,3]oxazino[3,2-a]indole-10-carboxamide as 5-HT(4) receptor antagonist
  申请人：SmithKline Beecham p.l.c.

  公开号：US20040176370A1

  公开（公告）日：2004-09-09

  3,4-Dihydro-N-[[1-(3-hydroxybutyl-4-piperidinyl]methyl]-2H-[1,3]oxazino[3,2-&agr;]indole-10-carboxamide and its use as 5-HT 4 receptor antagonist for example in the treatment or prophylaxis of gastrointestinal disorders, cardiovascular disorders and CNS disorders.

  3,4-二氢-N-[[1-(3-羟基丁基-4-哌啶基)甲基]-2H-[1,3]噁唑并[3,2-α]吲哚-10-羧酰胺及其作为5-HT4受体拮抗剂的用途，例如用于治疗或预防胃肠道疾病、心血管疾病和中枢神经系统疾病。
• Process for the preparation of an indole derivative
  申请人：SmithKline Beecham p.l.c.

  公开号：US20040192911A1

  公开（公告）日：2004-09-30

  A process for the preparation of methyl 2-(3-chloropropoxy)-indole-3-carboxylate, which comprises reacting a 3-chloro-3-carboxylate indole compound with 3-chloropropanol in the presence of an acid having a pKa of from 0 to 2.

  一种制备甲基2-(3-氯丙氧基)吲哚-3-羧酸甲酯的方法，包括在pKa值为0至2的酸存在下，将3-氯-3-羧酸吲哚化合物与3-氯丙醇反应。
• 5-HTX MODULATORS
  申请人：Klaveness Jo

  公开号：US20090029979A1

  公开（公告）日：2009-01-29

  This invention relates to compounds which bind to serotonin receptors inside or outside the central nervous system, in particular compounds which bind to the 5-HT 2 or 5-HT 7 receptors, their preparation and use, compositions containing them, and methods of treatment using them.

  本发明涉及与中枢神经系统内或外的血清素受体结合的化合物，特别是与5-HT2或5-HT7受体结合的化合物，其制备和使用，包含它们的组合物以及使用它们的治疗方法。
• Modulators of Preripheral 5-Ht Receptors
  申请人：Klaveness Jo

  公开号：US20070254874A1

  公开（公告）日：2007-11-01

  Novel modulators of 5-HT4 receptors have been developed which have a selectivity for peripheral receptors rather than those of the central nervous systems. Theses include novel derivatives of known modulators as well as entirely novel entities. Surprisingly, the derivatised compounds of the known modulators maintain a high binding affinity to 5-HT4 receptors, despite the presence of an acidic moiety at the end of an optional chain. The entirely novel entities also exhibit good binding affinity to 5-HT4 receptors. All of the compounds of the invention have a common motif which includes a basic nitrogen moiety and an acidic moiety. The compounds of the invention, due at least in part to their high ionisation potential at physiological pH, have the unique properties of selectively for peripheral 5HT4 receptors over those of the CNS, good binding affinity, and selectively of 5HT4 receptors over other serotonin receptors.

  已经开发出了5-HT4受体的新型调节剂，其选择性针对的是外周受体而非中枢神经系统受体。其中包括已知调节剂的新型衍生物以及全新的实体。令人惊讶的是，已知调节剂的衍生物化合物尽管在可选链的末端存在酸性基团，但仍保持对5-HT4受体的高结合亲和力。全新的实体也表现出良好的5-HT4受体结合亲和力。发明中的所有化合物都具有一个共同的基团，其中包括一种碱性氮基团和一种酸性基团。该发明中的化合物，至少部分原因是由于它们在生理pH值下具有高离化电位，具有选择性地作用于外周5-HT4受体而非中枢神经系统受体，具有良好的结合亲和力，并且对5-HT4受体的选择性高于其他血清素受体。