(S)-1-(2-Adamantan-1-yl-ethyl)-5-diphenylacetyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester | 150371-71-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-(2-Adamantan-1-yl-ethyl)-5-diphenylacetyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester
• 英文别名: methyl (6S)-1-[2-(1-adamantyl)ethyl]-5-(2,2-diphenylacetyl)-6,7-dihydro-4H-imidazo[4,5-c]pyridine-6-carboxylate
• CAS: 150371-71-4
• 化学式: C₃₄H₃₉N₃O₃
• 分子量: 537.702
• InChiKey: IJLQDCOLLWVUIL-PBTDNJIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-(2-Adamantan-1-yl-ethyl)-5-diphenylacetyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (S)-(diphenylacetyl)-4,5,6,7-tetrahydro-1-<2-(tricyclo<3.3.1.1^3,7>dec-1-yl)ethyl>-1H-imidazo<4.5-c>pyridine-6-carboxylic acid
  参考文献：
  名称：

  4,5,6,7-四氢-1 H-咪唑并[4,5 - c ]吡啶-6-羧酸（藤本碱）

  摘要：

  报道了天然存在的氨基酸4,5,6,7-四氢-1 H-咪唑并[4,5 - c ]吡啶-6-羧酸（斯皮纳辛）的新衍生物。这些包括酰胺，酯，5-烷基和酰基，和区域专一Ñ IM -烷基和芳烷基衍生物。描述了通过在N个im-取代的组氨酸上的Pictet-Spengler反应进行的合成。包括菠菜碱的环状乙内酰脲衍生物。

  DOI：

  10.1002/jhet.5570280118
• 作为产物：
  描述：

  (S)-5,6,7,8-tetrahydro-7-(methoxycarbonyl)-2-(2'-oxo-2'-phenylethyl)-5-oxoimidazo<1,5-c>pyrimidinium bromide 在 盐酸 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 89.75h， 生成 (S)-1-(2-Adamantan-1-yl-ethyl)-5-diphenylacetyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester
  参考文献：
  名称：

  4,5,6,7-四氢-1 H-咪唑并[4,5 - c ]吡啶-6-羧酸（藤本碱）

  摘要：

  报道了天然存在的氨基酸4,5,6,7-四氢-1 H-咪唑并[4,5 - c ]吡啶-6-羧酸（斯皮纳辛）的新衍生物。这些包括酰胺，酯，5-烷基和酰基，和区域专一Ñ IM -烷基和芳烷基衍生物。描述了通过在N个im-取代的组氨酸上的Pictet-Spengler反应进行的合成。包括菠菜碱的环状乙内酰脲衍生物。

  DOI：

  10.1002/jhet.5570280118

文献信息

• 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.
• 4,5,6,7-Tetrahydro-1<i>H</i>-imidazo[4,5-<i>c</i>]pyridine-6-carboxylic acids (spinacines)
  作者：Sylvester Klutchko、John C. Hodges、C. John Blankley、Norman L. Colbry

  DOI：10.1002/jhet.5570280118

  日期：1991.1

  New derivatives of the naturally occurring amino acid 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid (spinacine) are reported. These include amide, ester, 5-alkyl and acyl, and regiospecific Nim-alkyl and aralkyl derivatives. Synthesis via the Pictet-Spengler reaction on Nim-substituted histidines is described. Cyclic hydantoin derivatives of spinacines are included.

  报道了天然存在的氨基酸4,5,6,7-四氢-1 H-咪唑并[4,5 - c ]吡啶-6-羧酸（斯皮纳辛）的新衍生物。这些包括酰胺，酯，5-烷基和酰基，和区域专一Ñ IM -烷基和芳烷基衍生物。描述了通过在N个im-取代的组氨酸上的Pictet-Spengler反应进行的合成。包括菠菜碱的环状乙内酰脲衍生物。