4-(戊酰基氨基)苯甲酸 | 100390-76-9

• 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: 4-(戊酰基氨基)苯甲酸
• 英文名称: p-pentanamidobenzoic acid
• 英文别名: 4-(Pentanoylamino)benzoic acid
• CAS: 100390-76-9
• 化学式: C₁₂H₁₅NO₃
• mdl: MFCD01365923
• 分子量: 221.256
• InChiKey: SBQFPXHBAJDVLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  4-(戊酰基氨基)苯甲酸 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 氯化亚砜 、 硫酸 、 氢气 、 硝酸 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， -15.0~100.0 ℃ 、101.33 kPa 条件下， 反应 8.83h， 生成 肽U6
  参考文献：
  名称：

  Synthesis and antiaggregator activity of some new derivatives of 4H-1-benzopyran-4-one

  摘要：

  A series of 2-[2-alkyl-1H-benzimidazol-5(6)-yl]-4H-1 analogues 7a-7e was synthesized by the reaction with 3',4'-diaminoflavone and aliphatic carboxylic acids. 3',4'-Diaminoflavone 6 was prepared via the reduction of 2-(4-amino-3-nitrophenyl)-4H-1-benzopyran-4-one 5a. The compounds 7a-e and 14a-f were tested in vitro for their inhibitory activities against human platelet aggregation induced by collagen, ADP and A23187. The compound with a COOR group as a side chain, 2-(2-alkyloxycarbonyl-2,3-dihydro-1,4-benzodioxin-6-yl)-4H-1-benzopyran-4-one 14a-f, has potent activity, and so compound 13 was also prepared as an analogue of series 14 and tested for its antiaggregator activity.

  DOI：

  10.1016/0223-5234(96)88270-5
• 作为产物：
  描述：

  戊酰氯 在 甲醇 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 4-(戊酰基氨基)苯甲酸
  参考文献：
  名称：

  Synthesis, Structure–Activity Relationship, and Pharmacological Studies of Novel Melanin-Concentrating Hormone Receptor 1 Antagonists 3-Aminomethylquinolines: Reducing Human Ether-a-go-go-Related Gene (hERG) Associated Liabilities

  摘要：

  Recently, we discovered 3-aminomethylquinoline derivative 1, a selective, highly potent, centrally acting, and orally bioavailable human MCH receptor 1 (hMCHR1) antagonist, that inhibited food intake in F344 rats with diet-induced obesity (DIO). Subsequent investigation of 1 was discontinued because 1 showed potent hERG K+ channel inhibition in a patch-clamp study. To decrease hERG K+ channel inhibition, experiments with ligand-based drug designs based on 1 and a docking study were conducted. Replacement of the terminal p-fluorophenyl group with a cyclopropylmethoxy group, methyl group introduction on the benzylic carbon at the 3-position of the quinoline core, and employment of a [2-(acetylamino)ethyl]amino group as the amine portion eliminated hERG K+ channel inhibitory activity in a patch-clamp study, leading to the discovery of N-{3-[(1R)-1-{[2-(acetylamino)ethyl]amino}ethyl]-8-methylquinolin-7-yl}-4-(cyclopropylmethoxy)benzamide (R)-10h. The compound (R)-10h showed potent inhibitory activity against hMCHR1 and dose-dependently suppressed food intake in a 2-day study on DIO-F344 rats. Furthermore, practical chiral synthesis of (R)-10h was performed to determine the molecule's absolute configuration.

  DOI：

  10.1021/jm300167z