3-(4-苄基哌嗪-1-基)丙腈 | 198478-03-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(4-苄基哌嗪-1-基)丙腈
• 英文名称: 3-(4-benzylpiperazin-1-yl)propanenitrile
• CAS: 198478-03-4
• 化学式: C₁₄H₁₉N₃
• mdl: MFCD09860640
• 分子量: 229.325
• InChiKey: UMOVJHXZTBCGOB-UHFFFAOYSA-N

物化性质

• 沸点：
  380.6±32.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-苄基哌嗪-1-基)丙腈 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 1-(3-氨基丙基)-4-苄基哌嗪
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular docking study of novel piperidine and piperazine derivatives as multi-targeted agents to treat Alzheimer’s disease

  摘要：

  Development of Multi-Target Directed Ligands (MTDLs) has emerged as a promising approach for targeting complex etiology of Alzheimer's disease (AD). Following this approach, a new series of N'-(4-benzylpiperidin-/piperazin-/benzhydrylpiperazin-1-yl) alkylamine derivatives were designed, synthesized and biologically evaluated as inhibitors of cholinesterases (ChEs), amyloid-beta (A beta) self aggregation and also for their radical scavenging activity. The in vitro studies showed that the majority of synthesized derivatives strongly inhibited acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) with IC50 values in the low-nanomolar range, and were clearly more potent than the reference compound donepezil in this regard. Among them, inhibitors 5h and 5k, strongly inhibited AChE, with IC50 value of 6.83 nM and 2.13 nM, respectively, and particularly, compound 5k was found to be highly selective for AChE (similar to 38-fold). Moreover, both kinetic analysis of AChE inhibition and the docking study suggested that 5k binds simultaneously to catalytic active site and peripheral anionic site of AChE. Besides, these compounds also exhibited greater ability to inhibit self-induced A beta(1-42) aggregation at 25 mu M with percentage inhibition from similar to 54% to 89% and specially compound 5k provided highest inhibition (88.81%). Also, the derivatives containing methoxy and hydroxy groups showed potent oxygen radical absorbance capacity (ORAC) ranging from 2.2- to 4.4-fold of the Trolox value. Furthermore, results of ADMET studies suggested that all compounds exhibited appropriate drug like properties. Taken together, these results suggest that 5k might be a promising lead compound for further AD drug development. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.057
• 作为产物：
  描述：

  1-苄基哌嗪 、 丙烯腈 在 乙酸–三乙胺 作用下， 反应 0.02h， 以98%的产率得到3-(4-苄基哌嗪-1-基)丙腈
  参考文献：
  名称：

  醋酸 三乙铵（ TEAA）：一种可回收的廉价离子液体，可促进化学选择性的氮杂和 硫杂 迈克尔 反应

  摘要：

  用于化学选择性氮杂/硫杂一种新的，高效率的，廉价的，可回收，轻度，方便，和绿色协议 迈克尔 的胺/硫醇到α，β加成反应 - 使用三乙基乙酸铵（不饱和化合物 TEAA ）离子液体被开发。该催化剂可以循环使用十次，从而消除了对有毒和昂贵催化剂的需求。

  DOI：

  10.1007/s00706-008-0886-4

文献信息

• Ceric Ammonium Nitrate Catalyzed aza-Michael Addition of Aliphatic Amines to α,β-Unsaturated Carbonyl Compounds and Nitriles in Water
  作者：Srinivas Adapa、Ravi Varala、Nuvula Sreelatha

  DOI：10.1055/s-2006-941588

  日期：2006.6

  Ceric ammonium nitrate (3 mol%) efficiently catalyzes the aza-Michael reaction of amines with α,β-unsaturated carbonyl compounds in water to produce the corresponding β-amino carbonyl compounds in good to excellent yields (55-99%) for most of the compounds under mild conditions. The reaction is procedurally simple and displays limited chemoselectivity, as aromatic amines were found to be unreactive

  硝酸铈铵 (3 mol%) 可有效催化胺与水中 α,β-不饱和羰基化合物的氮杂-迈克尔反应，以良好至极好的收率（55-99%）生成相应的 β-氨基羰基化合物。化合物在温和条件下。该反应程序简单，并且显示出有限的化学选择性，因为发现芳香胺不具有反应性。
• Synthesis, characterization and in vitro biological studies of novel cyano derivatives of N-alkyl and N-aryl piperazine
  作者：Preeti Chaudhary、Surendra Nimesh、Veena Yadav、Akhilesh Kr. Verma、Rupesh Kumar

  DOI：10.1016/j.ejmech.2006.10.009

  日期：2007.4

  Cyano derivatives of N-alkyl and N-aryl piperazine have been synthesized and screened for antibacterial and antifungal activities. All the synthesized compounds showed the antibacterial activity against pathogenic strains of Staphylococcus aureus (MTCCB 737), Pseudomonas aeruginosa (MTCCB 741), Streptomyces epidermidis (MTCCB 1824) and Escherichia coli (MTCCB 1652) and antifungal activity against pathogenic

  已合成了N-烷基和N-芳基哌嗪的氰基衍生物，并筛选了其抗菌和抗真菌活性。所有合成的化合物均显示出对金黄色葡萄球菌（MTCCB 737），铜绿假单胞菌（MTCCB 741），表皮链霉菌（MTCCB 1824）和大肠杆菌（MTCCB 1652）的致病菌株的抗菌活性以及对曲霉（F. 4517），黄曲霉（ITCC 5192）和黑曲霉（ITCC 5405）。所有化合物均显示轻至中度的抗菌活性。但是，化合物3c，4a和6对研究中使用的致病菌株显示出强大的抗菌活性。化合物3a，3b，4b和4d对曲霉病原菌表现出轻度至中度的抗真菌活性。使用MTT比色测定法对Hela细胞评估了该研究中报道的化合物的细胞毒性。所有化合物均显示出比对照药物庆大霉素更高的细胞生存力，其中化合物2具有最高的细胞生存力，即95％。
• 5-memberd heteroaryl substituted 1,4-dihydropyridine compounds as bradykinin antagonists
  申请人：——

  公开号：US20010046993A1

  公开（公告）日：2001-11-29

  This invention provides a compound of the formula (I): 1 or the pharmaceutically acceptable salts thereof wherein A is independently halo; Y 1 is —(CH 2 ) m —, C(O) or S(O); Y 2 is N or CH; R 1 and R 2 are independently C 1-4 alkyl; R 3 is selected from the following: (a) optionally substituted —(CH 2 ) p —C 3-7 cycloalkyl; (b) optionally substituted —C 5-7 alkyl; and (c) substituted —C 1-4 alkyl; and (d) optionally substituted C 7- bicycloalkyl; R 4 is optionally substituted thiazolyl, imidazolyl or oxazolyl; X is S, —NH, —N—C 1-4 alkyl or O; R 5 is hydrogen or C 1-4 alkyl; R 6 is C 1-4 alkyl or halo; m is 0, 1 or 2; n is 0, 1, 2, 3, 4 or S; and p is 0, 1, 2, 3, 4, 5 or 6. These compounds are useful for the treatment of medical conditions caused by bradykinin such as inflammation, cardiovascular disease, pain, etc. This invention also provides a pharmaceutical composition comprising the above compound.

  这项发明提供了以下式(I)的化合物或其药学上可接受的盐，其中A独立地是卤素；Y1是—(CH2)m—、C(O)或S(O)；Y2是N或CH；R1和R2独立地是C1-4烷基；R3从以下选项中选择：(a) 可选地取代的—(CH2)p—C3-7环烷基；(b) 可选地取代的—C5-7烷基；以及(c) 取代的—C1-4烷基；和(d) 可选地取代的C7双环烷基；R4是可选地取代的噻唑基、咪唑基或噁唑基；X是S、—NH、—N—C1-4烷基或O；R5是氢或C1-4烷基；R6是C1-4烷基或卤素；m是0、1或2；n是0、1、2、3、4或S；p是0、1、2、3、4、5或6。这些化合物可用于治疗由激肽酶引起的医疗状况，如炎症、心血管疾病、疼痛等。该发明还提供了包含上述化合物的药物组合物。
• [EN] QUINAZOLINE DERIVATIVES<br/>[FR] DERIVES DE QUINAZOLINE
  申请人：ASTRAZENECA AB

  公开号：WO2002016352A1

  公开（公告）日：2002-02-28

  The invention concerns quinazoline derivatives of Formula (I) wherein each of m, R?1, n, R2 and R3¿ have any of the meanings defined in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an anti-invasive agent in the containment and/or treatment of solid tumour disease.

  本发明涉及式（I）的喹唑啉衍生物，其中m、R1、n、R2和R3中的每一个具有在说明书中定义的任何含义；它们的制备过程，包含它们的制药组合物以及它们在制造用于抗侵袭剂治疗和/或治疗实体瘤疾病的药物中的使用。
• Therapeutic use
  申请人：Moore Corine Nelly

  公开号：US20050014773A1

  公开（公告）日：2005-01-20

  The invention concerns the use of the quinazoline derivatives of Formula (I) Wherein each of m, R 1 , n, R 2 and R 3 have any of the meanings defined in the description in the manufacture of a medicament for use in the prevention or treatment of T cell mediated diseases or medical conditions such as autoimmune diseases like transplant rejection or rheumatoid arthritis in a warm-blooded animal.

  本发明涉及使用式（I）中的喹唑啉衍生物，在制备用于预防或治疗T细胞介导的疾病或医疗状况，例如自身免疫疾病，如移植排斥或类风湿性关节炎等热血动物的药物中，其中m，R1，n，R2和R3中的每一个具有描述中定义的任何含义。