6-amino-1-(3,4-dihydroquinolin-1(2H)-yl)hexan-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-amino-1-(3,4-dihydroquinolin-1(2H)-yl)hexan-1-one
• 英文别名: 6-amino-1-(3,4-dihydro-2H-quinolin-1-yl)hexan-1-one
• 化学式: C₁₅H₂₂N₂O
• 分子量: 246.352
• InChiKey: YOWOKDFMQSBIRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-amino-1-(3,4-dihydroquinolin-1(2H)-yl)hexan-1-one 在 三乙基硅烷 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 生成 N-(6-(3,4-dihydroquinolin-1(2H)-yl)-6-oxohexyl)-2-mercaptoacetamide trifluoroacetate
  参考文献：
  名称：

  Thiol-Based Potent and Selective HDAC6 Inhibitors Promote Tubulin Acetylation and T-Regulatory Cell Suppressive Function

  摘要：

  Several new mercaptoacetamides were synthesized and studied as HDAC6 inhibitors. One compound, 2b, bearing an aminoquinoline cap group, was found to show 1.3 nM potency at HDAC6, with >3000-fold selectivity over HDAC1. 2b also showed excellent efficacy at increasing tubulin acetylation in rat primary cortical cultures, inducing a 10-fold increase in acetylated tubulin at 1 mu M. To assess possible therapeutic effects, compounds were assayed for their ability to increase T-regulatory (Treg) suppressive function. Some but not all of the compounds increased Treg function, and thereby decreased conventional T cell activation and proliferation in vitro.

  DOI：

  10.1021/acsmedchemlett.5b00303
• 作为产物：
  描述：

  6-phthalimidohexanoyl chloride 在 水 、 N,N-二乙基苯胺 、 肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 6-amino-1-(3,4-dihydroquinolin-1(2H)-yl)hexan-1-one
  参考文献：
  名称：

  Synthesis of novel purin-6-yl conjugates with heterocyclic amines linked via 6-aminohexanoyl fragment

  摘要：

  Novel conjugates of purine and 2-aminopurine linked with heterocyclic amines, including chiral derivatives of 3,4-dihydro-2H-[1,4]benzoxazine, 3,4-dihydro-2H-[1,4]benzothiazine and 1,2,3,4-tetrahydroquinoline, by 6-aminohexanoyl fragment at the 6-position of purine moiety were obtained. For this purpose, replacement of the chlorine atom in 2-amino-6-chloropurine or 6-chloropurine by direct nucleophilic substitution reaction with 6-aminohexanamides or the coupling of 6-(purin-6-ylamino)-6-hexanoic acid with nitrogen heterocycles were used.

  DOI：

  10.1016/j.mencom.2015.11.003

文献信息

• [EN] BICYCLIC AND TRICYCLIC CAP BEARING MERCAPTOACETAMIDE DERIVATIVES AS HISTONE DEACETYLASE INHIBITORS<br/>[FR] DÉRIVÉS BICYCLIQUES ET TRICYCLIQUES DE MERCAPTOACÉTAMIDE COIFFÉS A TITRE D'INHIBITEURS D'HISTONES DÉSACÉTYLASES
  申请人：UNIV ILLINOIS

  公开号：WO2017053360A1

  公开（公告）日：2017-03-30

  Histone deacetylases inhibitors (HDACIs) and compositions containing the same are disclosed. Methods of treating diseases and conditions wherein inhibition of HDAC provides a benefit, like a cancer, a neurodegenerative disorder, a peripheral neuropathy, a neurological disease, traumatic brain injury, stroke, hypertension, malaria, an autoimmune disease, autism, autism spectrum disorders, and inflammation, also are disclosed.

  揭示了组蛋白去乙酰化酶抑制剂（HDACIs）及含有其的组合物。还揭示了治疗疾病和病况的方法，其中抑制HDAC提供益处，如癌症、神经退行性疾病、周围神经病变、神经系统疾病、创伤性脑损伤、中风、高血压、疟疾、自身免疫疾病、自闭症、自闭症谱系障碍和炎症。
• Thiol-Based Potent and Selective HDAC6 Inhibitors Promote Tubulin Acetylation and T-Regulatory Cell Suppressive Function
  作者：Mariana C. F. Segretti、Gian Paolo Vallerini、Camille Brochier、Brett Langley、Liqing Wang、Wayne W. Hancock、Alan P. Kozikowski

  DOI：10.1021/acsmedchemlett.5b00303

  日期：2015.11.12

  Several new mercaptoacetamides were synthesized and studied as HDAC6 inhibitors. One compound, 2b, bearing an aminoquinoline cap group, was found to show 1.3 nM potency at HDAC6, with >3000-fold selectivity over HDAC1. 2b also showed excellent efficacy at increasing tubulin acetylation in rat primary cortical cultures, inducing a 10-fold increase in acetylated tubulin at 1 mu M. To assess possible therapeutic effects, compounds were assayed for their ability to increase T-regulatory (Treg) suppressive function. Some but not all of the compounds increased Treg function, and thereby decreased conventional T cell activation and proliferation in vitro.
• Synthesis of novel purin-6-yl conjugates with heterocyclic amines linked via 6-aminohexanoyl fragment
  作者：Victor P. Krasnov、Dmitry A. Gruzdev、Evgeny N. Chulakov、Alexey Yu. Vigorov、Vera V. Musiyak、Tatyana V. Matveeva、Andrey A. Tumashov、Galina L. Levit、Valery N. Charushin

  DOI：10.1016/j.mencom.2015.11.003

  日期：2015.11

  Novel conjugates of purine and 2-aminopurine linked with heterocyclic amines, including chiral derivatives of 3,4-dihydro-2H-[1,4]benzoxazine, 3,4-dihydro-2H-[1,4]benzothiazine and 1,2,3,4-tetrahydroquinoline, by 6-aminohexanoyl fragment at the 6-position of purine moiety were obtained. For this purpose, replacement of the chlorine atom in 2-amino-6-chloropurine or 6-chloropurine by direct nucleophilic substitution reaction with 6-aminohexanamides or the coupling of 6-(purin-6-ylamino)-6-hexanoic acid with nitrogen heterocycles were used.