7-phenyl-5,7-diketoheptanoic acid | 268726-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-phenyl-5,7-diketoheptanoic acid
• 英文别名: 5,7-dioxo-7-phenyl-heptanoic acid；δ-Oxo-ε-benzoyl-capronsaeure；δ.ζ-Dioxo-ζ-phenyl-oenanthsaeure；4.6-Dioxo-6-phenyl-hexan-carbonsaeure-(1)；5,7-Dioxo-7-phenyl-heptansaeure；5,7-Dioxo-7-phenylheptanoic acid
• CAS: 268726-69-8
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: NJDUVFFGIGQTCU-UHFFFAOYSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  435.1±20.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-phenyl-5,7-diketoheptanoic acid 在 lithium aluminium tetrahydride 、 氯化亚砜 、 一水合肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 乙醇 为溶剂， 反应 11.0h， 生成 Dimethyl-[4-(5-phenyl-1H-pyrazol-3-yl)-butyl]-amine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel Pyrazoles and Indazoles as Activators of the Nitric Oxide Receptor, Soluble Guanylate Cyclase

  摘要：

  Database searching and compound screening identified 1-benzyl-3-(3-dimethylaminopropyloxy)-indazole (benzydamine, 3) as a potent activator of the nitric oxide receptor, soluble guanylate cyclase. A comprehensive structure-activity relationship study surrounding 3 clearly showed that the indazole C-3 dimethylaminopropyloxy substituent was critical for enzyme activity. However replacement of the indazole ring of 3 by appropriately substituted pyrazoles maintained enzyme activity. Compounds were evaluated for inhibition of platelet aggregation and showed a general lipophilicity requirement. Aryl-substituted pyrazoles 32, 34, and 43 demonstrated potent activation of soluble guanylate cyclase and potent inhibition of platelet aggregation. Pharmacokinetic studies in rats showed that compound 32 exhibits modest oral bioavailability (12%). Furthermore 32 has an excellent selectivity profile notably showing no significant inhibition of phosphodiesterases or nitric oxide synthases.

  DOI：

  10.1021/jm001034k
• 作为产物：
  描述：

  戊二酸酐 、 苯乙酮 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以66%的产率得到7-phenyl-5,7-diketoheptanoic acid
  参考文献：
  名称：

  The Synthesis and Characterization of a Novel Insulin Sensitizing Agent

  摘要：

  通过将芳基1,3-二酮与查尔酮缩合，我们开发了一条新颖简洁的2-羟基-4,6-二芳基二苯甲酮合成路线。所得化合物可刺激胰岛素依赖性葡萄糖进入脂肪细胞，并提高啮齿类糖尿病模型的胰岛素敏感性。

  DOI：

  10.1055/s-2004-825622

文献信息

• [EN] ACTIVATORS OF SOLUBLE GUANYLATE CYCLASE<br/>[FR] ACTIVATEURS DE GUANYLATE CYCLASE SOLUBLE
  申请人：UNIV LONDON

  公开号：WO2000027394A1

  公开（公告）日：2000-05-18

  The present invention describes the use of pyrazole or indazole derivates as activators of soluble guanylate cyclase. Some compounds disclosed are novel. All activators are vasodilators and/or inhibit platelet aggregation and are therefore useful in the treatment of peripheral vascular diseases such as hypertension, angina pectoris or atherosclerosis, or in the treatment of prevention of glaucoma, preeclampsia, Raynaud's syndrome, stroke or erectile disfunctions.

  本发明描述了将吡唑或吲唑衍生物用作可溶性鸟苷酸环化酶的激活剂。其中一些化合物是新颖的。所有激活剂均为血管扩张剂和/或抑制血小板聚集剂，因此可用于治疗外周血管疾病，如高血压、心绞痛或动脉粥样硬化，或用于预防青光眼、先兆子痫、雷诺综合征、中风或勃起功能障碍。
• Wieland; Drishaus, Justus Liebigs Annalen der Chemie, 1929, vol. 473, p. 109
  作者：Wieland、Drishaus

  DOI：——

  日期：——
• Synthesis and Biological Evaluation of Novel Pyrazoles and Indazoles as Activators of the Nitric Oxide Receptor, Soluble Guanylate Cyclase
  作者：David L. Selwood、David G. Brummell、Joanna Budworth、Guillaume E. Burtin、Richard O. Campbell、Surinder S. Chana、Ian G. Charles、Patricia A. Fernandez、Robert C. Glen、Maria C. Goggin、Adrian J. Hobbs、Marcel R. Kling、Qian Liu、David J. Madge、Sylvie Meillerais、Kenneth L. Powell、Karen Reynolds、Graham D. Spacey、Jeremy N. Stables、Mark A. Tatlock、Kerry A. Wheeler、Grant Wishart、Chi-Kit Woo

  DOI：10.1021/jm001034k

  日期：2001.1.1

  Database searching and compound screening identified 1-benzyl-3-(3-dimethylaminopropyloxy)-indazole (benzydamine, 3) as a potent activator of the nitric oxide receptor, soluble guanylate cyclase. A comprehensive structure-activity relationship study surrounding 3 clearly showed that the indazole C-3 dimethylaminopropyloxy substituent was critical for enzyme activity. However replacement of the indazole ring of 3 by appropriately substituted pyrazoles maintained enzyme activity. Compounds were evaluated for inhibition of platelet aggregation and showed a general lipophilicity requirement. Aryl-substituted pyrazoles 32, 34, and 43 demonstrated potent activation of soluble guanylate cyclase and potent inhibition of platelet aggregation. Pharmacokinetic studies in rats showed that compound 32 exhibits modest oral bioavailability (12%). Furthermore 32 has an excellent selectivity profile notably showing no significant inhibition of phosphodiesterases or nitric oxide synthases.
• The Synthesis and Characterization of a Novel Insulin Sensitizing Agent
  作者：Thomas W. von Geldern、Regina P. Brun、Masha Kalmanovich、Denise Wilcox、Peer B. Jacobson

  DOI：10.1055/s-2004-825622

  日期：——

  A novel and succinct route to 2-hydroxy-4,6-diarylbenzophenones has been developed through condensation of aryl 1,3-diketones with chalcones. The resultant compounds stimulate insulin-dependent glucose uptake into adipocytes, and improve insulin sensitivity in a rodent model of diabetes.

  通过将芳基1,3-二酮与查尔酮缩合，我们开发了一条新颖简洁的2-羟基-4,6-二芳基二苯甲酮合成路线。所得化合物可刺激胰岛素依赖性葡萄糖进入脂肪细胞，并提高啮齿类糖尿病模型的胰岛素敏感性。