(R)-N-((R)-5-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)-3-(naphthalene-2-sulfonamido)-3-phenylpropanamide | 925456-55-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-N-((R)-5-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)-3-(naphthalene-2-sulfonamido)-3-phenylpropanamide
• 英文别名: (3R)-N-[(1R)-5-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl]-3-(naphthalen-2-ylsulfonylamino)-3-phenylpropanamide
• CAS: 925456-55-9
• 化学式: C₂₉H₂₈N₂O₄S
• 分子量: 500.618
• InChiKey: FRMWLFSYEFSPGY-VSGBNLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-N-((R)-5-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)-3-(naphthalene-2-sulfonamido)-3-phenylpropanamide 在 manganese(IV) oxide 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 35.0h， 生成 (R)-3-(naphthalene-7-sulfonamido)-3-phenyl-N-((R)-5-(piperidin-1-ylmethyl)-2,3-dihydro-1H-inden-1-yl)propanamide
  参考文献：
  名称：

  Identification of a Nonpeptidic and Conformationally Restricted Bradykinin B1 Receptor Antagonist with Anti-Inflammatory Activity

  摘要：

  We report the discovery of chroman 28, a potent and selective antagonist of human, nonhuman primate, rat, and rabbit bradykinin B1 receptors (0.4-17 nM). At 90 mg/kg s.c., 28 decreased plasma extravasation in two rodent models of inflammation. A novel method to calculate entropy is introduced and ascribed similar to 30% of the gained affinity between "flexible" 4 (K-i = 132 nM) and "rigid" 28 (K-i = 0.77 nM) to decreased conformational entropy.

  DOI：

  10.1021/jm061224g
• 作为产物：
  描述：

  (R)-3-氨基-3-苯基丙酸盐酸盐 在 silica-supported carbodiimide 、 potassium carbonate 、 1-羟基苯并三唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 生成 (R)-N-((R)-5-(hydroxymethyl)-2,3-dihydro-1H-inden-1-yl)-3-(naphthalene-2-sulfonamido)-3-phenylpropanamide
  参考文献：
  名称：

  Identification of a Nonpeptidic and Conformationally Restricted Bradykinin B1 Receptor Antagonist with Anti-Inflammatory Activity

  摘要：

  We report the discovery of chroman 28, a potent and selective antagonist of human, nonhuman primate, rat, and rabbit bradykinin B1 receptors (0.4-17 nM). At 90 mg/kg s.c., 28 decreased plasma extravasation in two rodent models of inflammation. A novel method to calculate entropy is introduced and ascribed similar to 30% of the gained affinity between "flexible" 4 (K-i = 132 nM) and "rigid" 28 (K-i = 0.77 nM) to decreased conformational entropy.

  DOI：

  10.1021/jm061224g

文献信息

• Identification of a Nonpeptidic and Conformationally Restricted Bradykinin B1 Receptor Antagonist with Anti-Inflammatory Activity
  作者：Derin C. D'Amico、Toshi Aya、Jason Human、Christopher Fotsch、Jian Jeffrey Chen、Kaustav Biswas、Bobby Riahi、Mark H. Norman、Christopher A. Willoughby、Randall Hungate、Paul J. Reider、Gloria Biddlecome、Dianna Lester-Zeiner、Carlo Van Staden、Eileen Johnson、Augustus Kamassah、Leyla Arik、Judy Wang、Vellarkad N. Viswanadhan、Robert D. Groneberg、James Zhan、Hideo Suzuki、Andras Toro、David A. Mareska、David E. Clarke、Darren M. Harvey、Laurence E. Burgess、Ellen R. Laird、Benny Askew、Gordon Ng

  DOI：10.1021/jm061224g

  日期：2007.2.1

  We report the discovery of chroman 28, a potent and selective antagonist of human, nonhuman primate, rat, and rabbit bradykinin B1 receptors (0.4-17 nM). At 90 mg/kg s.c., 28 decreased plasma extravasation in two rodent models of inflammation. A novel method to calculate entropy is introduced and ascribed similar to 30% of the gained affinity between "flexible" 4 (K-i = 132 nM) and "rigid" 28 (K-i = 0.77 nM) to decreased conformational entropy.