1-(2,6-dimethylbenzoyl)piperidine-4-one | 306296-68-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2,6-dimethylbenzoyl)piperidine-4-one
• 英文别名: 1-(2,6-dimethylbenzoyl)piperidin-4-one；N-(2,6-dimethylbenzoyl)-4-piperidinone；N-(2,6-dimethylbenzoyl)4-piperidone；1-(2,6-Dimethyl-benzoyl)-piperidin-4-one
• CAS: 306296-68-4
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: BQOOUKMOGICWOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2,6-dimethylbenzoyl)piperidine-4-one 在 盐酸 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (3R)-1-[1-(2,6-dimethylbenzoyl)piperidin-4-yl]pyrrolidin-3-amine
  参考文献：
  名称：

  WO2007/116313

  摘要：

  公开号：
• 作为产物：
  描述：

  2,6-二甲基苯甲酸 在 N-甲基吗啉 、 盐酸 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 1-(2,6-dimethylbenzoyl)piperidine-4-one
  参考文献：
  名称：

  WO2007/116313

  摘要：

  公开号：

文献信息

• Piperazine derivatives useful as CCR5 antagonists
  申请人：Schering Corporation

  公开号：US06391865B1

  公开（公告）日：2002-05-21

  The use of CCR5 antagonists of the formula or a pharmaceutically acceptable salt thereof, wherein R is optionally substituted phenyl, pyridyl, thiophenyl or naphthyl; R1 is hydrogen or alkyl; R2 is substituted phenyl, substituted heteroaryl, naphthyl, fluorenyl, diphenylmethyl or optionally substituted phenyl- or heteroaryl-alkyl; R3 is hydrogen, alkyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, or optionally substituted phenyl, phenylalkyl, naphthyl, naphthylalkyl, heteroaryl or heteroarylalkyl; R4, R5 and R7 are hydrogen or alkyl; R6 is hydrogen, alkyl or alkenyl; for the treatment of HIV, solid organ transplant rejection, graft v. host disease, arthritis, rheumatoid arthritis, inflammatory bowel disease, atopic dermatitis, psoriasis, asthma, allergies or multiple sclerosis is disclosed, as well as novel compounds, pharmaceutical compositions comprising them, and the combination of CCR5 antagonists of the invention in combination with antiviral agents useful in the treatment of HIV or agents useful in the treatment of inflammatory diseases.

  公开了使用CCR5拮抗剂的公式，其中 R是可选择的取代苯基，吡啶基，噻吩基或萘基; R1是氢或烷基; R2是取代苯基，取代杂环基，萘基，芴基，二苯甲基或可选择的取代苯基或杂环基烷基; R3是氢，烷基，烷氧基烷基，环烷基，环烷基烷基，或可选择的取代苯基，苯基烷基，萘基，萘基烷基，杂环基或杂环基烷基; R4，R5和R7是氢或烷基; R6是氢，烷基或烯基; 用于治疗HIV，固体器官移植排斥，移植物宿主病，关节炎，类风湿关节炎，炎症性肠病，特应性皮炎，牛皮癣，哮喘，过敏或多发性硬化症的方法，以及包含它们的新化合物，包含它们的药物组合物，以及CCR5拮抗剂与抗HIV治疗中有用的抗病毒剂或与治疗炎症性疾病中有用的药物的组合。
• Heterocyclic antiviral compounds
  申请人：Gabriel Deems Stephen

  公开号：US20050176703A1

  公开（公告）日：2005-08-11

  This invention relates to piperidine derivatives of formulae Ia and Ib with substituents as defined herein useful in the treatment of a variety of disorders, including those in which the modulation of CCR5 receptors is implicated. More particularly, the present invention relates to 1-oxa-3,8-diaza-spiro[4.5]decan-2-one and 1-oxa-3,9-diaza-spiro[5.5]undecan-2-one compounds and related derivatives, to compositions containing and to uses of such derivatives. Disorders that may be treated or prevented by the present derivatives include HIV and genetically related retroviral infections (and the resulting acquired immune deficiency syndrome, AIDS), diseases of the immune system and inflammatory diseases.

  本发明涉及式Ia和式Ib的哌啶衍生物，其取代基的定义如下，可用于治疗多种疾病，包括那些涉及CCR5受体调节的疾病。更具体地，本发明涉及1-氧杂-3,8-二氮杂-螺[4.5]癸烷-2-酮和1-氧杂-3,9-二氮杂-螺[5.5]十一烷-2-酮化合物及其相关衍生物，包括含有这些衍生物的组合物和这些衍生物的用途。本衍生物可用于治疗或预防HIV和遗传相关的逆转录病毒感染（以及由此引起的获得性免疫缺陷综合症，艾滋病），免疫系统疾病和炎症性疾病。
• CHEMICAL COMPOUNDS
  申请人：Barber Christopher Gordon

  公开号：US20090124636A1

  公开（公告）日：2009-05-14

  The present invention provides compounds of formula (I) wherein R 1 to R 6 and m are as defined hereinabove. The compounds of the present invention are modulators, especially antagonists, of the activity of chemokine CCR5 receptors. Modulators of the CCR5 receptor may be useful in the treatment of various inflammatory diseases, autoimmune diseases, pain, and. in the treatment of infection by HIV and genetically related retroviruses.

  本发明提供公式（I）中R1至R6和m如上所定义的化合物。本发明的化合物是趋化因子CCR5受体活性的调节剂，特别是拮抗剂。CCR5受体的调节剂可能在治疗各种炎症性疾病、自身免疫性疾病、疼痛以及治疗HIV和遗传相关的逆转录病毒感染方面有用。
• The design and discovery of novel amide CCR5 antagonists
  作者：David C. Pryde、Martin Corless、David R. Fenwick、Helen J. Mason、Blanda C. Stammen、Peter T. Stephenson、David Ellis、David Bachelor、David Gordon、Christopher G. Barber、Anthony Wood、Donald S. Middleton、David C. Blakemore、Gemma C. Parsons、Rachel Eastwood、Michelle Y. Platts、Keith Statham、Kerry A. Paradowski、Catherine Burt、Wolfgang Klute

  DOI：10.1016/j.bmcl.2009.01.012

  日期：2009.2

  The synthesis of a range of novel amine-containing structures and their primary potency as inhibitors of HIV-1 fusion via blocking of the CCR5 receptor is described. The development of the medicinal chemistry strategy and SAR's which led to the identification of the piperidine amide compounds 33 and 36 as excellent leads for further evaluation is described, along with key physicochemical data which highlighted their lead potential. (C) 2009 Elsevier Ltd. All rights reserved.
• Structural Modifications to Tetrahydropyridine-3-carboxylate Esters en Route to the Discovery of M₅-Preferring Muscarinic Receptor Orthosteric Antagonists
  作者：Guangrong Zheng、Andrew M. Smith、Xiaoqin Huang、Karunai L. Subramanian、Kiran B. Siripurapu、Agripina Deaciuc、Chang-Guo Zhan、Linda P. Dwoskin

  DOI：10.1021/jm301774u

  日期：2013.2.28

  The M-5 muscarinic acetylcholine receptor is suggested to be a potential pharmacotherapeutic target for the treatment of drug abuse. We describe herein the discovery of a series of M-5-preferring orthosteric antagonists based on the scaffold of 1,2,5,6-tetrahydropyridine-3-carboxylic acid. Compound 56, the most selective compound in this series, possesses an 11-fold selectivity for the M-5 over M-1 receptor and shows little activity at M-2-M-4. This compound, although exhibiting modest affinity (K-i = 2.24 mu M) for the [H-3]N-methylscopolamine binding site on the M-5 receptor, is potent (IC50 = 0.45 nM) in inhibiting oxotremorine-evoked [H-3]DA release from rat striatal slices. Further, a homology model of human M-5 receptor based on the crystal structure of the rat M-3 receptor was constructed, and docking studies of compounds 28 and 56 were performed in an attempt to understand the possible binding mode of these novel analogues to the receptor.