(S)-4,5,6,7-tetrahydro-1-[(4-methoxy-3-methylphenyl)methyl]-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester | 114955-85-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-4,5,6,7-tetrahydro-1-[(4-methoxy-3-methylphenyl)methyl]-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester
• 英文别名: methyl (6S)-1-[(4-methoxy-3-methylphenyl)methyl]-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-6-carboxylate
• CAS: 114955-85-0
• 化学式: C₁₇H₂₁N₃O₃
• 分子量: 315.372
• InChiKey: YPTWKEQYBCFIRN-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4,5,6,7-tetrahydro-1-[(4-methoxy-3-methylphenyl)methyl]-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester 在 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 50.0h， 生成 (S)-(-)-4,5,6,7-tetrahydro-1-[(4-methoxy-3-methylphenyl)methyl]-5-(phenylacetyl)-1H-imidazo-[4,5-c]pyridine-6-carboxylic acid
  参考文献：
  名称：

  Synthesis and structure-activity relationships of a novel series of non-peptide angiotensin II receptor binding inhibitors specific for the AT2 subtype

  摘要：

  Structure-activity relationships are reported for a novel class of 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid derivatives that displace I-125-labeled angiotensin II from a specific subset of angiotensin II (Ang II) binding sites in rat adrenal preparations. This binding site is not the Ang II receptor mediating vascular contraction or aldosterone release, but, rather, is one whose function has not yet been fully elucidated. It has been identified in a number of tissues and has a similar affinity for Ang II and its peptide analogues as does the vascular receptor. The non-peptide compounds reported here are uniquely specific in displacing Ang II at this binding site and are inactive in antagonizing Ang II at the vascular receptor or in pharmacological assays measuring vascular effects. PD 123,319 (79), one of the most potent compounds, has an IC50 of 34 nM. Certain of these compounds may have utility in the definition and study of Ang II receptor subtypes.

  DOI：

  10.1021/jm00115a014
• 作为产物：
  描述：

  N-<(1,1-dimethylethoxy)carbonyl>-3-<(3-methyl-4-nitrophenyl)methyl>-L-histidine methyl ester 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 27.5h， 生成 (S)-4,5,6,7-tetrahydro-1-[(4-methoxy-3-methylphenyl)methyl]-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and structure-activity relationships of a novel series of non-peptide angiotensin II receptor binding inhibitors specific for the AT2 subtype

  摘要：

  Structure-activity relationships are reported for a novel class of 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid derivatives that displace I-125-labeled angiotensin II from a specific subset of angiotensin II (Ang II) binding sites in rat adrenal preparations. This binding site is not the Ang II receptor mediating vascular contraction or aldosterone release, but, rather, is one whose function has not yet been fully elucidated. It has been identified in a number of tissues and has a similar affinity for Ang II and its peptide analogues as does the vascular receptor. The non-peptide compounds reported here are uniquely specific in displacing Ang II at this binding site and are inactive in antagonizing Ang II at the vascular receptor or in pharmacological assays measuring vascular effects. PD 123,319 (79), one of the most potent compounds, has an IC50 of 34 nM. Certain of these compounds may have utility in the definition and study of Ang II receptor subtypes.

  DOI：

  10.1021/jm00115a014

文献信息

• 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid analogs
  申请人：Warner-Lambert Company

  公开号：US04812462A1

  公开（公告）日：1989-03-14

  This invention relates to novel substituted derivatives of 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid and analogs thereof, which are useful for the treatment of hypertension, as well as, novel pharmaceutical compositions and methods of use.

  本发明涉及4,5,6,7-四氢-1H-咪唑[4,5-c]吡啶-6-羧酸及其衍生物的新置换衍生物，这些衍生物对高血压的治疗有用，以及新的药物组合物和使用方法。
• 4,5,6,7-Tetrahydro-1H-imidazo[4,5-c]pyridine derivatives and analogs having antihypertensive activity
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0245637A1

  公开（公告）日：1987-11-19

  This invention relates to novel substituted derivatives of 4,5,6,7-tetrahydro-1H-imidazo [4,5-c]-pyridine and analogs thereof, which are useful for the treatment of hypertension, as well as, novel pharmaceutical compositions and methods of use.

  本发明涉及可用于治疗高血压的 4,5,6,7- 四氢-1H-咪唑并[4,5-c]-吡啶的新型取代衍生物及其类似物，以及新型药物组合物和使用方法。
• US4812462A
  申请人：——

  公开号：US4812462A

  公开（公告）日：1989-03-14
• US4816463A
  申请人：——

  公开号：US4816463A

  公开（公告）日：1989-03-28
• Synthesis and structure-activity relationships of a novel series of non-peptide angiotensin II receptor binding inhibitors specific for the AT2 subtype
  作者：C. John Blankley、John C. Hodges、Sylvester R. Klutchko、Richard J. Himmelsbach、Alexander Chucholowski、Cleo J. Connolly、Sandra J. Neergaard、Michael S. Van Nieuwenhze、Alan Sebastian

  DOI：10.1021/jm00115a014

  日期：1991.11

  Structure-activity relationships are reported for a novel class of 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid derivatives that displace I-125-labeled angiotensin II from a specific subset of angiotensin II (Ang II) binding sites in rat adrenal preparations. This binding site is not the Ang II receptor mediating vascular contraction or aldosterone release, but, rather, is one whose function has not yet been fully elucidated. It has been identified in a number of tissues and has a similar affinity for Ang II and its peptide analogues as does the vascular receptor. The non-peptide compounds reported here are uniquely specific in displacing Ang II at this binding site and are inactive in antagonizing Ang II at the vascular receptor or in pharmacological assays measuring vascular effects. PD 123,319 (79), one of the most potent compounds, has an IC50 of 34 nM. Certain of these compounds may have utility in the definition and study of Ang II receptor subtypes.