1H-咪唑并[4,5-c]吡啶-6-羧酸,5-(二苯乙酰)-4,5,6,7-四氢-1-[(3-甲基-4-硝基苯基)甲基]-,甲基酯,(S)- | 114785-70-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1H-咪唑并[4,5-c]吡啶-6-羧酸,5-(二苯乙酰)-4,5,6,7-四氢-1-[(3-甲基-4-硝基苯基)甲基]-,甲基酯,(S)-
• 英文名称: (S)-5-(diphenylacetyl)-4,5,6,7-tetrahydro-1-<(3-methyl-4-nitrophenyl)methyl>-1H-imidazo<4,5-c>pyridine-6-carboxylic acid methyl ester
• 英文别名: (S)-5-diphenylacetyl-1-(3-methyl-4-nitrophenyl)methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester；methyl (6S)-5-(2,2-diphenylacetyl)-1-[(3-methyl-4-nitrophenyl)methyl]-6,7-dihydro-4H-imidazo[4,5-c]pyridine-6-carboxylate
• CAS: 114785-70-5
• 化学式: C₃₀H₂₈N₄O₅
• 分子量: 524.576
• InChiKey: QNHIZJFWWFCQMO-MHZLTWQESA-N

物化性质

• 熔点：
  168-171 °C
• 沸点：
  759.1±60.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1H-咪唑并[4,5-c]吡啶-6-羧酸,5-(二苯乙酰)-4,5,6,7-四氢-1-[(3-甲基-4-硝基苯基)甲基]-,甲基酯,(S)- 在 镍 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 以100%的产率得到(S)-1-<(4-amino-3-methylphenyl)-methyl>-5-(diphenylacetyl)-4,5,6,7-tetrahydro-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
• 作为产物：
  描述：

  3-(3-甲基-4-硝基苄基)-L-组氨酸二盐酸 在 盐酸 、 聚合甲醛 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 1H-咪唑并[4,5-c]吡啶-6-羧酸,5-(二苯乙酰)-4,5,6,7-四氢-1-[(3-甲基-4-硝基苯基)甲基]-,甲基酯,(S)-
  参考文献：
  名称：

  4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid amide

  摘要：

  本文揭示了具有高拮抗活性对抗血管紧张素II和对抗血管紧张素II受体具有高特异性的4,5,6,7-四氢-1H-咪唑[4,5-c]吡啶-6-羧酸酰胺衍生物，用于制备这些衍生物的中间体，以及包括这些衍生物的抗血管紧张素II拮抗剂。

  公开号：

  US05401736A1

文献信息

• 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid amide
  申请人：Kureha Kagaku Kogyo Kabushiki Kaisha

  公开号：US05401736A1

  公开（公告）日：1995-03-28

  Disclosed herein are 4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid amide derivatives having a high antagonistic activity against angiotensin II and a high specificity to angiotensin II receptors, intermediates for preparing the derivatives, and antagonists against angiotensin II comprising the derivatives.

  本文揭示了具有高拮抗活性对抗血管紧张素II和对抗血管紧张素II受体具有高特异性的4,5,6,7-四氢-1H-咪唑[4,5-c]吡啶-6-羧酸酰胺衍生物，用于制备这些衍生物的中间体，以及包括这些衍生物的抗血管紧张素II拮抗剂。
• 4,5,6,7-Tetrahydro-1H-imidazo 4,5-c pyridine-6-carboxylic acid amide derivatives as angiotensine II antagonistes
  申请人：KUREHA KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0589665A2

  公开（公告）日：1994-03-30

  A compound of formula (I): or a pharmaceutically acceptable salt thereof; wherein R¹ represents    hydrogen,    halogen,    C₁-C₆ alkyl,    C₃-C₆ alkenyl,    C₃-C₆ alkynyl,    R²⁰(CH₂)n- wherein R²⁰ represents C₃-C₈ cycloalkyl, naphthyl, phenyl, or phenyl substituted with one to five of C₁-C₄ alkyl, halogen atom, trifluoromethyl, hydroxy, C₁-C₄ alkoxy, C₁-C₃ acyloxy, amino, N-mono-C₁-C₄ alkylamino, N-di-C₁-C₄ alkylamino, C₁-C₄ thioalkyl, C₁-C₃ alkylsulfonyl, nitro, and -NHCOR²¹ wherein R²¹ represents C₁-C₃ alkyl, phenyl, C₁-C₃ alkylphenyl, aminophenyl, or C₁-C₄ alkylaminophenyl, and n is an integer of 1 to 6,    R²⁰-C(O)- wherein R²⁰ is as defined above, or    R²⁰-CH(OH)- wherein R²⁰ is as defined above; R² represents carbamoyl, mono- or di-C₁-C₆ alkylcarbamoyl, or 4- to 6-membered heterocyclic carbamoyl; R represents amino, carboxy, (1H-tetrazol-5-yl)phenyl, carboxyphenyl, carboxybenzamido, (1H-tetrazol-5-yl)benzamido, carboxyphenylcarbamoyl, or (1H-tetrazol-5-yl)-phenylcarbamoyl; R³ represents -CH₂(phenyl), -CH(phenyl)₂, -CH(phenyl)CH₃, -CH(phenyl) (cyclohexyl), -CH₂CH₂(phenyl), -CH₂(C₁-C₆ alkoxyphenyl), or -CH₂(hydroxyphenyl); and R⁴, R⁷, and R⁸ each independently represents hydrogen or C₁-C₆ alkyl, is an angiotensin II antagonist.

  式 (I) 的化合物： 或其药学上可接受的盐；其中 R¹ 代表 氢 卤素 C₁-C₆ 烷基 C₃-C₆ 烯基、 C₃-C₆ 烷基、 R²⁰(CH₂)n- 其中 R²⁰ 代表 C₃-C₈ 环烷基、萘基、苯基或被 1 至 5 个 C₁-C₄ 烷基取代的苯基、卤素原子、三氟甲基、羟基、C₁-C₄ 烷氧基、C₁-C₃酰氧基、氨基、N-单-C₁-C₄ 烷基氨基、N-二-C₁-C₄烷基氨基、C₁-C₄硫烷基、C₁-C₃烷基磺酰基、硝基和-NHCOR²¹，其中 R²¹ 代表 C₁-C₃烷基、苯基、C₁-C₃ 烷基苯基、氨基苯基或 C₁-C₄ 烷氨基苯基，且 n 为 1-6 的整数、 R²⁰-C(O)- 其中 R²⁰ 如上定义，或 R²⁰-CH(OH)- 其中 R²⁰ 如上定义； R² 代表氨基甲酰基、单-或双-C₁-C₆ 烷基氨基甲酰基或 4-6 元杂环氨基甲酰基； R 代表氨基、羧基、(1H-四唑-5-基)苯基、羧基苯基、羧基苯甲酰胺基、(1H-四唑-5-基)苯甲酰胺基、羧基苯基氨基甲酰基或 (1H-四唑-5-基)-苯基氨基甲酰基； R³ 代表-CH₂(苯基)、-CH(苯基)₂、-CH(苯基)CH₃、-CH(苯基)(环己基)、-CH₂CH₂(苯基)、-CH₂(C₁-C₆烷氧基苯基)或-CH₂(羟基苯基)；以及 R⁴、R⁷ 和 R⁸ 各自独立地代表氢或 C₁-C₆ 烷基，是血管紧张素 II 拮抗剂。
• US5401736A
  申请人：——

  公开号：US5401736A

  公开（公告）日：1995-03-28
• 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.