1-[3-(4-甲基-1-哌嗪)-苯基]-乙酮 | 56915-80-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[3-(4-甲基-1-哌嗪)-苯基]-乙酮
• 英文名称: 1-[3-(4-methylpiperazin-1-yl)phenyl]ethanone
• 英文别名: 1-(3-acetylphenyl)-4-methylpiperazine；1-[3-(4-methyl-piperazin-1-yl)-phenyl]-ethanone；m-(4-methyl-1-piperazinyl)acetophenone；m-<4-Methyl-1-piperazinyl>acetophenon；m-(4-Methyl-1-piperazinyl)acetophenon
• CAS: 56915-80-1
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: UOADBNQWYZHSLK-UHFFFAOYSA-N

物化性质

• 沸点：
  361.5±37.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[3-(4-甲基-1-哌嗪)-苯基]-乙酮 在 乙醇 、 盐酸羟胺 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 生成 [1-[3-(4-methylpiperazin-1-yl)phenyl]ethylideneamino] piperidine-1-carboxylate
  参考文献：
  名称：

  Identification of a novel arylpiperazine scaffold for fatty acid amide hydrolase inhibition with improved drug disposition properties

  摘要：

  We herein describe the systematic approach used to develop new analogues of compound 2, recently identified as a potent and selective fatty acid amide hydrolase (FAAH) inhibitor. Aiming at identifying new scaffolds endowed with improved drug disposition properties with respect to the phenylpyrrole-based lead, we subjected it to two different structural modification strategies. This process allowed the identification of derivatives 4b and 5c as potent, reversible and non-competitive FAAH inhibitors. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.11.035
• 作为产物：
  描述：

  3'-溴苯乙酮 在 盐酸 、 tris(dibenzylideneacetone)dipalladium (0) 、 对甲苯磺酸 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 38.0h， 生成 1-[3-(4-甲基-1-哌嗪)-苯基]-乙酮
  参考文献：
  名称：

  Cationic Chalcone Antibiotics. Design, Synthesis, and Mechanism of Action

  摘要：

  This paper describes how the introduction of "cationic" aliphatic amino groups in the chalcone scaffold results in potent antibacterial compounds. It is shown that the most favorable position for the aliphatic amino group is the 2-position of the B-ring, in particular in combination with a lipophilic substituent in the 5-position of the beta-ring. We demonstrate that the compounds act by unselective disruption of cell membranes. Introduction of an additional aliphatic amino group in the A-ring results in compounds that are selective for bacterial membranes combined with a high antibacterial activity against both Gram-positive and -negative pathogens. The most potent compound in this study (78) has an MIC value of 2 mu M against methicillin resistant Staphylococus aureus.

  DOI：

  10.1021/jm049424k

文献信息

• [EN] 3, 4-DISUBSTITUTED 1H-PYRAZOLE COMPOUNDS AND THEIR USE AS CYCLIN DEPENDENT KINASES (CDK) AND GLYCOGEN SYNTHASE KINASE-3 (GSK-3) MODULATORS<br/>[FR] COMPOSES 1H-PYRAZOLE 3,4-DISUBSTITUES ET LEUR UTILISATION EN TANT QUE KINASES DEPENDANT DES CYCLINES (CDK) ET MODULATEURS DE LA GLYCOGENE SYNTHASE KINASE-3 (GSK-3)
  申请人：ASTEX TECHNOLOGY LTD

  公开号：WO2005012256A1

  公开（公告）日：2005-02-10

  The invention provides compounds of the formula (0) or salts or tautomers or N-oxides or solvates thereof for use in the prophylaxis or treatment of disease states and conditions such as cancers mediated by cyclin-dependent kinase and glycogen synthase kinase-3. Formula (0). In formula (0): X is a group R1-A-NR4- or a 5- or 6-membered carbocyclic or heterocyclic ring; A is a bond, S02, C=O, NRg(C=O) or O(C=O) wherein Rg is hydrogen or C1-4 hydrocarbyl optionally substituted by hydroxy or C1-4 alkoxy; Y is a bond or an alkylene chain of 1, 2 or 3 carbon atoms in length; R1 is hydrogen; a carbocyclic or heterocyclic group having from 3 to 12 ring members; or a C1-8 hydrocarbyl group optionally substituted by one or more substituents selected from halogen (e.g. fluorine), hydroxy, C1-4 hydrocarbyloxy, amino, mono- or di-C1-4 hydrocarbylamino, and carbocyclic or heterocyclic groups having from 3 to 12 ring members, and wherein 1 or 2 of the carbon atoms of the hydrocarbyl group may optionally be replaced by an atom or group selected from 0, S, NH, SO, S02; R2 is hydrogen; halogen; C1-4 alkoxy (e.g. methoxy); or a C1-4 hydrocarbyl group optionally substituted by halogen (e.g. fluorine), hydroxyl or C1-4 alkoxy (e.g. methoxy); R3 is selected from hydrogen and carbocyclic and heterocyclic groups having from 3 to 12 ring members; and R4 is hydrogen or a C1-4 hydrocarbyl group optionally substituted by halogen (e.g. fluorine), hydroxyl or C1-4 alkoxy (e.g. methoxy).

  该发明提供了以下式（0）的化合物或其盐或互变异构体或N-氧化物或其溶剂合物，用于预防或治疗由细胞周期依赖性激酶和糖原合成酶-3介导的癌症等疾病状态和病症。在式（0）中：X是一个基团R1-A-NR4-或一个5-或6-成员的碳环或杂环；A是一个键，S02，C=O，NRg（C=O）或O（C=O），其中Rg是氢或C1-4烃基，可以选择性地被羟基或C1-4烷氧基取代；Y是一个键或一个由1、2或3个碳原子组成的烷基链；R1是氢；一个具有3到12个环成员的碳环或杂环基团；或一个C1-8烃基，可以选择性地被卤素（如氟）、羟基、C1-4烷氧基、氨基、单或双C1-4烃基氨基以及具有3到12个环成员的碳环或杂环基团取代，其中烃基的1或2个碳原子可以选择性地被从0、S、NH、SO、S02中选择的原子或基团所取代；R2是氢；卤素；C1-4烷氧基（如甲氧基）；或一个C1-4烃基，可以选择性地被卤素（如氟）、羟基或C1-4烷氧基（如甲氧基）取代；R3从氢和具有3到12个环成员的碳环或杂环基团中选择；R4是氢或一个C1-4烃基，可以选择性地被卤素（如氟）、羟基或C1-4烷氧基（如甲氧基）取代。
• Novel antibacterial amide compounds and process means for producing the
  申请人：Parke, Davis & Company

  公开号：US03954734A1

  公开（公告）日：1976-05-04

  Novel organic amide compounds which are N-[6-[(substituted amino)phenyl]-1,2-dihydro-2-oxonicotinyl]penicillin and cephalosporin type compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate penicillin or cephalosporin or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding N-6-[(substituted amino)phenyl]-1,2-dihydro-2-oxonicotinic acid or (b) reacting the free amino acid 6-amino-penicillanic acid, 7-aminocephalosporanic acid, 7-amino-3-methylceph-3-em-4-carboxylic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[6-[(substituted amino)phenyl]-1,2-dihydro-2-oxonicotinyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.

  提供了一种新型的有机酰胺化合物，即N-[6-[(取代氨基)苯基]-1,2-二氢-2-氧基烟酰基]青霉素和头孢菌素类化合物，具有广谱抗菌作用，方法包括(a)将适当青霉素或头孢菌素的游离氨基酸或其酸盐或硅烷衍生物与相应的N-6-[(取代氨基)苯基]-1,2-二氢-2-氧基烟酸的反应衍生物反应，或(b)将游离氨基酸6-氨基青霉素酸、7-氨基头孢菌素酸、7-氨基-3-甲基头孢-3-酮-4-羧酸或相关化合物或其酸盐或硅烷衍生物与相应的D-N-[6-[(取代氨基)苯基]-1,2-二氢-2-氧基烟酰基]-2-取代甘氨酸的反应衍生物反应。还公开了含有上述化合物的药物组合物以及使用这些组合物治疗感染的方法。
• A new class of histone deacetylase inhibitors
  申请人：DAC S.r.l.

  公开号：EP2033956A1

  公开（公告）日：2009-03-11

  This invention is related to new histone deacetylase inhibitors according to the general formula (I) wherein: Q is a bond, CH2, NR5 or oxygen, X is CH or nitrogen, Y is a bond, CH2, oxygen or NR6, Z is CH or nitrogen, R1, R2 are, independently, hydrogen or C1-C6 alkyl, R3, R4 are, independently, hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl or C1-C6 haloalkoxy, and R5 and R6 are as further defined in the specification, and pharmaceutical acceptable salts thereof.

  这项发明涉及新的组蛋白去乙酰化酶抑制剂，其通式为（I），其中：Q是键，CH2，NR5或氧，X是CH或氮，Y是键， ，氧或NR6，Z是CH或氮，R1，R2分别是氢或C1-C6烷基，R3，R4分别是氢，卤素，C1-C6烷基，C1-C6烷氧基，C1-C6卤代烷基或C1-C6卤代烷氧基，R5和R6的进一步定义在说明书中，并且其药用盐是可以接受的。
• Combinations of Pyrazole Kinase Inhibitors and Further Antitumor Agents
  申请人：Curry Jayne Elizabeth

  公开号：US20080161355A1

  公开（公告）日：2008-07-03

  The invention provides a combination of a compound having the formula (0) and two or more further anti-cancer agents: or salts or tautomers or N-oxides or solvates thereof; wherein X is a group R 1 -A-NR 4 — or a 5- or 6-membered carbocyclic or heterocyclic ring; A is a bond, SO2, C═O, NR 9 (C═O) or 0(C═O) wherein R 9 is hydrogen or C 1-4 hydrocarbyl optionally substituted by hydroxy or C 1-4 alkoxy; Y is a bond or an alkylene chain of 1, 2 or 3 carbon atoms in length; R 1 is hydrogen; a carbocyclic or heterocyclic group having from 3 to 12 ring members; or a C 1-8 hydrocarbyl group optionally substituted by one or more substituents selected from halogen (e.g. fluorine), hydroxy, C 1-4 hydrocarbyloxy, amino, mono- or di-C 1-4 hydrocarbylamino, and carbocyclic or heterocyclic groups having from 3 to 12 ring members, and wherein 1 or 2 of the carbon atoms of the hydrocarbyl group may optionally be replaced by an atom or group selected from O, S, NH, SO, SO 2 ; R 2 is hydrogen; halogen; C 1-4 alkoxy (e.g. methoxy); or a C 1-4 hydrocarbyl group optionally substituted by halogen (e.g. fluorine), hydroxyl or C 1-4 alkoxy (e.g. methoxy); R 3 is selected from hydrogen and carbocyclic and heterocyclic groups having from 3 to 12 ring members; and R 4 is hydrogen or a C 1-4 hydrocarbyl group optionally substituted by halogen (e.g. fluorine), hydroxyl or C 1-4 alkoxy (e.g. methoxy).

  本发明提供了一种由具有公式（0）的化合物和两种或更多进一步的抗癌剂组成的组合物：或其盐或互变异构体或N-氧化物或溶剂化物；其中X是一个R1-A-NR4-或一个5-或6-成员的碳环或杂环环；A是一个键，SO2，C═O，NR9（C═O）或0（C═O），其中R9是氢或C1-4烃基，可以选择地被羟基或C1-4烷氧基取代；Y是一个键或长度为1、2或3个碳原子的烷基链；R1是氢；具有3到12个环成员的碳环或杂环基团；或者是一个C1-8烃基，可以选择地被一个或多个取代基所取代，所述取代基选自卤素（例如氟）、羟基、C1-4烃氧基、氨基、单-或双C1-4烃基氨基和具有从3到12个环成员的碳环或杂环基团，其中烃基的1或2个碳原子可以选择性地被O、S、NH、SO、SO2中的一个原子或基取代；R2是氢；卤素；C1-4烷氧基（例如甲氧基）；或一个C1-4烃基，可以选择地被卤素（例如氟）、羟基或C1-4烷氧基（例如甲氧基）所取代；R3选自氢和具有从3到12个环成员的碳环和杂环基团；R4是氢或一个C1-4烃基，可以选择地被卤素（例如氟）、羟基或C1-4烷氧基（例如甲氧基）所取代。
• Pharmaceutical Compounds
  申请人：Curry Jayne Elizabeth

  公开号：US20080161251A1

  公开（公告）日：2008-07-03

  The invention provides a combination of a cytotoxic compound or signalling inhibitor and a compound having the formula (0): or salts or tautomers or N-oxides or solvates thereof; wherein X is a group R 1 -A-NR 4 - or a 5- or 6-membered carbocyclic or heterocyclic ring; A is a bond, SO 2 , C═O, NR g (C═O) or 0(C═O) wherein R g is hydrogen or C 1-4 hydrocarbyl optionally substituted by hydroxy or C 1-4 alkoxy; Y is a bond or an alkylene chain of 1, 2 or 3 carbon atoms in length; R 1 is hydrogen; a carbocyclic or heterocyclic group having from 3 to 12 ring members; or a C 1-8 hydrocarbyl group optionally substituted by one or more substituents selected from halogen (e.g. fluorine), hydroxy, C 1-4 hydrocarbyloxy, amino, mono- or di-C 1-4 hydrocarbylamino, and carbocyclic or heterocyclic groups having from 3 to 12 ring members, and wherein 1 or 2 of the carbon atoms of the hydrocarbyl group may optionally be replaced by an atom or group selected from O, S, NH, SO, SO 2 ; R 2 is hydrogen; halogen; C 1-4 alkoxy (e.g. methoxy); or a C 1-4 hydrocarbyl group optionally substituted by halogen (e.g. fluorine), hydroxyl or C 1-4 alkoxy (e.g. methoxy); R 3 is selected from hydrogen and carbocyclic and heterocyclic groups having from 3 to 12 ring members; and R 4 is hydrogen or a C 1-4 hydrocarbyl group optionally substituted by halogen (e.g. fluorine), hydroxyl or C 1-4 alkoxy (e.g. methoxy).

  本发明提供了一种细胞毒性化合物或信号抑制剂与式(0)的化合物或其盐、互变异构体、N-氧化物或溶剂化物的组合物；其中X是一个R1-A-NR4-或5-或6-成员的碳环或杂环；A是一个键，SO2，C═O，NRg(C═O)或0(C═O)，其中Rg是氢或C1-4羟基或C1-4烷氧基取代的烷基；Y是一个键或1、2或3个碳原子长的烷基链；R1是氢；一个从3到12个环成员的碳环或杂环基团；或一个C1-8烷基基团，可选地取代一个或多个取代基，所述取代基选自卤素（例如氟）、羟基、C1-4烷氧基、氨基、C1-4单取代或双取代烷基氨基和从3到12个环成员的碳环或杂环基团，其中烷基基团的1或2个碳原子可以选为O、S、NH、SO或SO2中的原子或基团；R2是氢；卤素；C1-4烷氧基（例如甲氧基）；或一个C1-4烷基基团，可选地取代卤素（例如氟）、羟基或C1-4烷氧基（例如甲氧基）；R3选自氢和从3到12个环成员的碳环或杂环基团；R4是氢或一个C1-4烷基基团，可选地取代卤素（例如氟）、羟基或C1-4烷氧基（例如甲氧基）。