(R)-3-(1-(3-fluoro-5-(3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyridin-2-yl)ethyl)-1-hydroxy-1-methylurea | 1217888-71-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (R)-3-(1-(3-fluoro-5-(3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyridin-2-yl)ethyl)-1-hydroxy-1-methylurea
• 英文别名: 3-[(1R)-1-[3-fluoro-5-[3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyridin-2-yl]ethyl]-1-hydroxy-1-methylurea
• CAS: 1217888-71-5
• 化学式: C₁₈H₁₇F₂N₅O₃
• 分子量: 389.361
• InChiKey: XHEYWMUWFZPSKT-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N,N'-二琥珀酰亚胺基碳酸酯 、 N-甲基羟胺 、 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 生成 (R)-3-(1-(3-fluoro-5-(3-fluoro-2-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyridin-2-yl)ethyl)-1-hydroxy-1-methylurea
  参考文献：
  名称：

  Novel small molecule bradykinin B1 receptor antagonists. Part 3: Hydroxyurea derivatives

  摘要：

  Hydroxy urea moieties are introduced as a new class of bradykinin B-1 receptor antagonists. First, the SAR of the lead compound was systematically explored. Subsequent optimization resulted in the identification of several biaryl-based hydroxyurea bradykinin B-1 receptor antagonists with low-nanomolar activity and very high oral bioavailability in the rat. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.121

文献信息

• [EN] SMALL MOLECULE BRADYKININ B1 RECEPTOR ANTAGONISTS<br/>[FR] PETITES MOLÉCULES ANTAGONISTES DU RÉCEPTEUR B1 DE LA BRADYKININE
  申请人：JERINI AG

  公开号：WO2010091876A2

  公开（公告）日：2010-08-19

  The present invention is related to a compound of the formula (I): or a pharmacologically acceptable salt, solvate or hydrate thereof, wherein A is formula (II) (III) (IV), X is Ch or N; R1, R2, R3, R4, R6, R7, and R8 are each and independently of each other selected from hydrogen atom, halogen atom, hydroxy, cyano, amino, alkyl, or optionally substituted heteroalkyl; R5 is a halogen atom, hydroxy, cyano, amino, an alkyl, an optionally substituted heteroalkyl, an optionally substituted cycloalkyl, an optionally substituted heterocycloalkyl, an optionally substituted alkylcycloalkyl, an optionally substituted heteroalkylcycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteroaralkyl; R9 is a hydrogen atom, an alkyl, or a heteroalkyl; R10 is a hydrogen atom, an alkyl, an optionally substituted heteroalkyl, an optionally substituted cycloalkyl, an optionally substituted heterocycloalkyl, an optionally substituted aralkyl, or an optionally substituted heteroaralkyl; R11 is an alkyl, an optionally substituted heteroalkyl, an optionally substituted cycloalkyl, an optionally substituted heterocycloalkyl, an optionally substituted alkylcycloalkyl, an optionally substituted heteroalkylcycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteroaralkyl; R12 is a hydrogen atom, an alkyl, an optionally substituted heteroalkyl, an optionally substituted cycloalkyl, an optionally substituted heterocycloalkyl, an optionally substituted aryl, an optionally substituted aralkyl, or an optionally substituted heteroaralkyl; B is O or N; Z1 and Z2 are each and independently of each other selected from C or N, and Z3 and Z4 are each and independently of each other selected from C, S, O or N; R13 is an alkyl, an optionally substituted heteroalkyl, an optionally substituted cycloalkyl, an optionally substituted heterocycloalkyl, an optionally substituted alkylcycloalkyl, an optionally substituted heteroalkylcycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted aralkyl, or an optionally substituted heteroaralkyl; R14 and R15, if present, are (i) each and independently of each other selected from hydrogen atom, halogen atom, CN, hydroxy, =O, alkyl, C3-C6-cycloalkyl, heteroalkyl or alkoxy; or (ii) joined together to form a carbocyclic or heterocyclic 5- or 6-membered ring, which is substituted with 0 to 4 substituents selected from the group comprising R16, R17, R18 and R19, and is saturated, unsaturated, or aromatic, and, if heterocyclic, contains one or more heteroatom(s) each and independently selected from N, O and S; and R16, R17, R18 and R19 are individually and independently selected from hydrogen atom, halogen atom, hydroxy, cyano, amino, alkyl, and optionally substituted heteroalkyl.
• Novel small molecule bradykinin B1 receptor antagonists. Part 3: Hydroxyurea derivatives
  作者：Karsten Schnatbaum、Marco Schaudt、Roland Stragies、Jochen R. Pfeifer、Christoph Gibson、Elsa Locardi、Dirk Scharn、Uwe Richter、Holger Kalkhof、Klaus Dinkel、Gunther Zischinsky

  DOI：10.1016/j.bmcl.2009.11.121

  日期：2010.2

  Hydroxy urea moieties are introduced as a new class of bradykinin B-1 receptor antagonists. First, the SAR of the lead compound was systematically explored. Subsequent optimization resulted in the identification of several biaryl-based hydroxyurea bradykinin B-1 receptor antagonists with low-nanomolar activity and very high oral bioavailability in the rat. (C) 2009 Elsevier Ltd. All rights reserved.