2-hydroxybenzaldehyde | 811867-22-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-hydroxybenzaldehyde
• 英文别名: tert-butyl N-[2-[2-[2-[tert-butyl(dimethyl)silyl]oxyethoxy]phenyl]ethyl]carbamate
• CAS: 811867-22-8
• 化学式: C₂₁H₃₇NO₄Si
• 分子量: 395.615
• InChiKey: UTPHPFHVTDCBHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxybenzaldehyde 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到2-hydroxybenzaldehyde
  参考文献：
  名称：

  Intermediates for macrocyclic compounds

  摘要：

  本发明涉及一种新型的大环化合物，其化学式为（I），以及其药用可接受的盐、水合物或溶剂化合物：其中R1、R2、R3、R4、R5、R6、n1、m、p、Z1、Z2和Z3如规范中所描述。该发明还涉及化合物的化学式（I），这些化合物是胃动素受体拮抗剂，可用于治疗与该受体相关的疾病以及与胃肠动力功能障碍相关的疾病。

  公开号：

  US09181298B2
• 作为产物：
  描述：

  2-(2-nitroethyl)phenol 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-hydroxybenzaldehyde
  参考文献：
  名称：

  Optimization of the Potency and Pharmacokinetic Properties of a Macrocyclic Ghrelin Receptor Agonist (Part I): Development of Ulimorelin (TZP-101) from Hit to Clinic

  摘要：

  High-throughput screening of Tranzyme Pharma's proprietary macrocycle library using the aequorin Ca2+-bioluminescence assay against the human ghrelin receptor (GRLN) led to the discovery of novel ago fists against this G-protein coupled receptor. Early hits such as 1 (K-i = 86 nM, EC50 = 134 nM) though potent in vitro displayed poor pharmacokinetic properties that required optimization. While such macrocycles are not fully rule-of-five compliant, principally due to their molecular weight and clogP, optimization of their pharmacokinetic properties proved feasible largely through conformational rigidification. Extensive SAR led to the identification of 2 (K-i = 16 nM, EC50 = 29 nM), also known as ulimorelin or TZP-101, which has progressed to phase III human clinical trials for the treatment of postoperative ileus. X-ray structure and detailed NMR studies indicated a rigid peptidomimetic portion in 2 that is best defined as a nonideal type-I' beta-turn. Compound 2 is 24% orally bioavailable in both rats and monkeys. Despite its potency, in vitro and in gastric emptying studies, 2 did not induce growth hormone (GH) release in rats, thus demarcating the GH versus GI pharmacology of GRLN.

  DOI：

  10.1021/jm2007062