2H-吖庚英-2-酮,六氢-7-(2-丙烯基)- | 165385-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 中文名称: 2H-吖庚英-2-酮,六氢-7-(2-丙烯基)-
• 英文名称: hexahydro-7-(2-propenyl)-1H-azepin-2-one
• 英文别名: 7-prop-2-enylazepan-2-one
• CAS: 165385-96-6
• 化学式: C₉H₁₅NO
• mdl: MFCD03085971
• 分子量: 153.224
• InChiKey: PEQHDCZVPRQCHM-UHFFFAOYSA-N

物化性质

• 熔点：
  97-99 °C(Solv: heptane (142-82-5); toluene (108-88-3))
• 沸点：
  295.1±9.0 °C(Predicted)
• 密度：
  0.923±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2H-吖庚英-2-酮,六氢-7-(2-丙烯基)- 在 氯化铵 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 hexahydro-7-(2-propenyl)-1H-azepin-2-imine, monohydrochloride
  参考文献：
  名称：

  2-Iminohomopiperidinium Salts as Selective Inhibitors of Inducible Nitric Oxide Synthase (iNOS)

  摘要：

  An attractive approach to the treatment of inflammatory conditions such as osteo-and rheumatoid arthritis, inflammatory bowel disease, and sepsis is through the selective inhibition of human inducible nitric oxide synthase (hiNOS) since localized excess nitric oxide (NO) release has been implicated in the pathology of these diseases. A series of monosubstituted iminohomopiperidinium salts possessing lipophilic functionality at ring positions 3, 5, 6, and 7 has been synthesized, and series members have demonstrated the ability to inhibit the hiNOS isoform with an IC50 as low as 160 nM (7). Compounds were found that selectively inhibit hiNOS over the human endothelial constitutive enzyme (heNOS) with a heNOS/hiNOS IC50 ratio in excess of 100 and as high as 314 (9). Potencies for inhibition of hiNOS and the human neuronal constitutive enzyme (hnNOS) are comparable. Substitution in the 3 and 7 positions provides compounds that exhibit the greatest degree of selectivity for hiNOS and hnNOS over heNOS. Submicromolar potencies for 6 and 7 in a mouse RAW cell assay demonstrated the ability of these compounds to inhibit iNOS in a cellular environment. These latter compounds were also found to be orally bioavailable and efficacious due to their ability to inhibit the increase in plasma nitrite/nitrate levels in a rat LPS model.

  DOI：

  10.1021/jm9704715
• 作为产物：
  描述：

  2-(2'-丙烯基)环己酮肟 在 sodium hydroxide 、 苯磺酰氯 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 生成 2H-吖庚英-2-酮,六氢-7-(2-丙烯基)-
  参考文献：
  名称：

  Khan, A. R.; McCarthy, T J.; Welch, M. J., Journal of labelled compounds and radiopharmaceuticals, 2001, vol. 44, p. S298 - S300

  摘要：

  DOI：

文献信息

• Carbocyclic Amino Ketones by Bredt's Rule‐Arrested Kulinkovich–de Meijere Reaction
  作者：Paul B. Finn、Brenden P. Derstine、Scott McN. Sieburth

  DOI：10.1002/anie.201509983

  日期：2016.2.12

  reaction, involves two carbon–carbon bond‐forming steps. Strategic use of a tricyclic intermediate can arrest the process if the second step requires formation of a bridgehead double bond. Use of this Bredt's rule constraint results in the production of carbocyclic amino ketones, key alkaloid building blocks.

  Ti II介导的由烯烃和酰胺形成的环丙胺，Kulinkovich-de Meijere反应涉及两个碳-碳键形成步骤。如果第二步需要形成桥头双键，则三环中间体的战略性使用可中止该过程。使用此Bredt规则约束会产生碳环氨基酮（关键生物碱构件）的产生。
• Compounds for Treating Disorders Mediated by Metabotropic Glutamate Receptor 5, and Methods of Use Thereof
  申请人：Hardy Larry Wendell

  公开号：US20110319380A1

  公开（公告）日：2011-12-29

  Provided herein are compounds and methods of synthesis thereof. The compounds set forth herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders, neurodegenerative disorders, neuropsychiatric disorders, disorders of cognition, learning or memory, gastrointestinal disorders, lower urinary tract disorder, and cancer. Compounds set forth herein modulate the activity of metabotropic glutamate receptor 5 (mGluR5) in the central nervous system or the periphery. Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.

  本文提供了化合物及其合成方法。本文中提供的化合物可用于治疗、预防和/或管理各种疾病，如神经系统疾病、神经退行性疾病、神经精神疾病、认知、学习或记忆障碍、胃肠道疾病、下尿路障碍和癌症。本文提供的化合物在中枢神经系统或外周调节代谢性谷氨酸受体5(mGluR5)的活性。本文还提供了含有这些化合物的药物制剂及其使用方法。
• COMPOUNDS FOR TREATING DISORDERS MEDIATED BY METABOTROPIC GLUTAMATE RECEPTOR 5, AND METHODS OF USE THEREOF
  申请人：Sunovion Pharmaceuticals Inc.

  公开号：US20140349992A1

  公开（公告）日：2014-11-27

  Provided herein are compounds and methods of synthesis thereof. The compounds set forth herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders, neurodegenerative disorders, neuropsychiatric disorders, disorders of cognition, learning or memory, gastrointestinal disorders, lower urinary tract disorder, and cancer. Compounds set forth herein modulate the activity of metabotropic glutamate receptor 5 (mGluR5) in the central nervous system or the periphery. Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.

  本文提供了化合物及其合成方法。这些化合物可用于治疗、预防和/或管理各种疾病，如神经疾病、神经退行性疾病、神经精神疾病、认知、学习或记忆障碍、胃肠道疾病、下尿路障碍和癌症等。本文提供的化合物在中枢神经系统或外周调节代谢性谷氨酸受体5 (mGluR5) 的活性。本文还提供了含有这些化合物的药物制剂及其使用方法。
• Amidino derivatives useful as nitric oxide synthase inhibitors
  申请人：G.D. SEARLE & CO.

  公开号：EP0897912A1

  公开（公告）日：1999-02-24

  The current invention discloses useful pharmaceutical compositions containing amidino derivatives of formula (I) as nitric oxide synthase inhibitors.

  本发明公开了含有式（I）脒基衍生物作为一氧化氮合酶抑制剂的有用药物组合物。
• Compositions and kits for enzymatic debridement and methods of using the same
  申请人：ROCHAL INDUSTRIES, LLC

  公开号：US10238719B2

  公开（公告）日：2019-03-26

  A debridement enzyme for necrotic tissue is described that is not dependent upon proteolytic enzymatic activity but instead utilizes the amylase family of enzymes. The amylases (α-, β-, γ-amylase) are noted for the cleavage of the α-glycosidic bonds of polysaccharides, yielding lower molecular weight carbohydrate/sugar fragments. It has now been found that α-amylase is effective in the debridement of devitalized tissue.

  描述了一种用于坏死组织的清创酶，这种酶不依赖于蛋白水解酶活性，而是利用淀粉酶家族的酶。淀粉酶（α-、β-、γ-淀粉酶）以裂解多糖的 α-糖苷键而著称，可产生分子量较低的碳水化合物/糖片段。现已发现，α-淀粉酶能有效地清除坏死组织。