Methyl 1,2,3,4-tetrahydro-6-(1H-indol-3-ylmethyl)-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate | 491614-16-5

• 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 1,2,3,4-tetrahydro-6-(1H-indol-3-ylmethyl)-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate
• 英文别名: methyl 6-(1H-indol-3-ylmethyl)-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate
• CAS: 491614-16-5
• 化学式: C₂₂H₂₃N₃O₄S
• 分子量: 425.508
• InChiKey: BHXRCGAOSYHMSG-UHFFFAOYSA-N

物化性质

• 沸点：
  646.2±65.0 °C(Predicted)
• 密度：
  1.323±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 1,2,3,4-tetrahydro-6-(1H-indol-3-ylmethyl)-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1,2,3,4-Tetrahydro-6-(1H-indol-3-ylmethyl)-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylic acid
  参考文献：
  名称：

  Potent blockers of the monocarboxylate transporter MCT1: Novel immunomodulatory compounds

  摘要：

  A novel series of potent blockers of the monocarboxylate transporter, MCT1, is disclosed. From very potent but lipophilic lead compounds, systematic changes to all parts of the molecule, targeting reduction in log D, afforded compounds with significantly improved overall properties. These Compounds show potent immunomodulatory activity. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.024
• 作为产物：
  描述：

  methyl 6-bromomethyl-1-isobutyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carboxylate 、 吲哚 在 碳酸氢钠 作用下， 以 氯仿 为溶剂， 以63%的产率得到Methyl 1,2,3,4-tetrahydro-6-(1H-indol-3-ylmethyl)-3-methyl-1-(2-methylpropyl)-2,4-dioxothieno[2,3-d]pyrimidine-5-carboxylate
  参考文献：
  名称：

  Potent blockers of the monocarboxylate transporter MCT1: Novel immunomodulatory compounds

  摘要：

  A novel series of potent blockers of the monocarboxylate transporter, MCT1, is disclosed. From very potent but lipophilic lead compounds, systematic changes to all parts of the molecule, targeting reduction in log D, afforded compounds with significantly improved overall properties. These Compounds show potent immunomodulatory activity. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.024

文献信息

• Chemical compounds
  申请人：——

  公开号：US20040171623A1

  公开（公告）日：2004-09-02

  The invention relates to a compound of formula (1)(A chemical formula should be inserted here—please see paper copy enclosed) wherein Q is —CO— or —C(R 4 )(R 5 )— (wherein R 4 is a hydrogen atom or C 1-4 alkyl and R 5 is a hydrogen atom or hydroxy group) and Ar is a 5- to 10-membered aromatic ring system wherein up to 4 ring atoms may be heteroatoms independently selected from nitrogen, oxygen and sulphur, the ring system being optionally substituted by one or more substituents as defined in the specification. It also relates to methods of preparing, pharmaceutical compositions containing and methods of using the compound of the formula (1), particularly in the modulation of autoimmune disease. 1

  本发明涉及一种式为（1）的化合物（化学式应在此处插入-请参见附上的纸质副本），其中Q为-CO-或-C（R4）（R5）-（其中R4为氢原子或C1-4烷基，R5为氢原子或羟基），Ar为一个5-至10-成员的芳香环系统，其中最多4个环原子可以是氮、氧和硫的杂原子，该环系统可以被定义在规范中的一种或多种取代基替换。本发明还涉及制备该式（1）化合物的方法，含有该化合物的药物组合物以及使用该化合物的方法，特别是在自身免疫性疾病的调节中。
• Chemical Compounds
  申请人：Reynolds Rachel Heulwen

  公开号：US20080153855A1

  公开（公告）日：2008-06-26

  The invention relates to a compound of formula (1) in which Q is —CO— or —C(R 4 )(R 5 )—, where R 4 is a hydrogen atom or C 1-4 alkyl and R 5 is a hydrogen atom or hydroxy group; and Ar is a 5- to 10-membered aromatic ring system where up to 4 ring atoms may be heteroatoms independently selected from nitrogen, oxygen and sulphur, the ring system being optionally substituted by one or more substituents as defined in the specification. It also relates to methods of preparing, pharmaceutical compositions containing and methods of using the compound of the formula (1), particularly in the modulation of autoimmune disease.

  本发明涉及一种化合物，其化学式为（1），其中Q为—CO—或—C（R4）（R5）—，其中R4为氢原子或C1-4烷基，R5为氢原子或羟基；Ar为一个5-到10-成员的芳香环系，其中最多4个环原子可以是氮、氧和硫的杂原子，该环系可以被定义在规范中的一个或多个取代基所取代。本发明还涉及制备方法、含有该化合物的药物组合物以及使用该化合物的方法，特别是在自身免疫性疾病的调节方面。
• THIENO¬2,3-d|PYRIMIDINEDIONES AS INHIBITORS OF T-CELLS PROLIFERATION
  申请人：AstraZeneca AB

  公开号：EP1412362B1

  公开（公告）日：2006-08-02
• US7361660B2
  申请人：——

  公开号：US7361660B2

  公开（公告）日：2008-04-22
• Potent blockers of the monocarboxylate transporter MCT1: Novel immunomodulatory compounds
  作者：S.D. Guile、J.R. Bantick、D.R. Cheshire、M.E. Cooper、A.M. Davis、D.K. Donald、R. Evans、C. Eyssade、D.D. Ferguson、S. Hill、R. Hutchinson、A.H. Ingall、L.P. Kingston、I. Martin、B.P. Martin、R.T. Mohammed、C. Murray、M.W.D. Perry、R.H. Reynolds、P.V. Thorne、D.J. Wilkinson、J. Withnall

  DOI：10.1016/j.bmcl.2006.01.024

  日期：2006.4

  A novel series of potent blockers of the monocarboxylate transporter, MCT1, is disclosed. From very potent but lipophilic lead compounds, systematic changes to all parts of the molecule, targeting reduction in log D, afforded compounds with significantly improved overall properties. These Compounds show potent immunomodulatory activity. (C) 2006 Elsevier Ltd. All rights reserved.