1-苄基哌嗪-2-羧酸乙酯 | 134749-45-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 1-苄基哌嗪-2-羧酸乙酯
• 英文名称: ethyl 1-benzylpiperazine-2-carboxylate
• 英文别名: 1-(phenylmethyl)-2-piperazinecarboxylic acid ethyl ester；1-benzyl-piperazinee-2-carboxylic acid ethyl ester；1-benzyl-piperazine-2-carboxylic acid ethyl ester；1-Benzyl-2-(ethoxycarbonyl)piperazine；ethyl 1-benzyl piperazine-2-carboxylate；ethyl 1-benzyl-piperazine-2-carboxylate
• CAS: 134749-45-4
• 化学式: C₁₄H₂₀N₂O₂
• 分子量: 248.325
• InChiKey: IAEHFMBLCHNXJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  1,4-二苄基哌嗪-2-羧酸乙酯	ethyl 1,4-dibenzylpiperazin-2-carboxylate	72351-59-8	C21H26N2O2	338.45
  ——	Ethyl 1-benzyl-4-tritylpiperazine-2-carboxylate	604785-27-5	C33H34N2O2	490.645
  ——	1-tritylpiperazin-3yl-carboxylic acid ethyl ester	162510-56-7	C26H28N2O2	400.521

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  1-苄基-4-甲基哌嗪-2-羧酸乙酯	ethyl 1-benzyl-4-methylpiperazine-2-carboxylate	63285-59-6	C15H22N2O2	262.352
  (1-苄基哌嗪-2-基)甲醇	(1-benzyl-piperazin-2-yl)-methanol	476493-27-3	C12H18N2O	206.288
  ——	1-benzyl-2-ethoxycarbonyl-4-[1-(pyridin-4-yl)piperidin-4-ylcarbonyl]piperazine	——	C25H32N4O3	436.554
  ——	ethyl 1-benzyl-4-(2-naphthylsulphonyl)piperazine-2-carboxylate	——	C24H26N2O4S	438.547
  ——	ethyl 1-benzyl-4-(6-bromo-2-naphthylsulphonyl)piperazine-2-carboxylate	——	C24H25BrN2O4S	517.443
  ——	4-[(chloro-2-naphthalenyl)sulfonyl]-1-(phenylmethyl)-2-piperazinecarboxylic acid ethyl ester	229647-15-8	C24H25ClN2O4S	472.993

反应信息

• 作为反应物：
  描述：

  1-苄基哌嗪-2-羧酸乙酯 在 palladium on activated charcoal 氨 、 氢气 、 碳酸氢钠 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， -75.0~25.0 ℃ 、275.79 kPa 条件下， 反应 7.0h， 生成 8-(trifluoromethylsulfonyl)octahydropyrazino<1,2-a>pyrazine-1,4-dione
  参考文献：
  名称：

  Gubert; Braojos; Sacristan, Synthesis, 1991, # 4, p. 318 - 320

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 1,4-bis(phenylmethyl)-2-piperazine carboxylate dihydrochloride 在 palladium on activated charcoal 盐酸 、 氢气 、 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 18.0h， 生成 1-苄基哌嗪-2-羧酸乙酯
  参考文献：
  名称：

  Design and Synthesis of Imidazoline Derivatives Active on Glucose Homeostasis in a Rat Model of Type II Diabetes. 1. Synthesis and Biological Activities of N-Benzyl-N ‘-(arylalkyl)-2-(4‘,5‘-dihydro-1‘H-imidazol-2‘-yl)piperazines

  摘要：

  The physiopathology of non-insulin-dependent diabetes mellitus is associated with a dysfunction in the regulation of insulin secretion. The alpha(2)-adrenoceptors have been reported to be involved in this alteration, although at-antagonists containing an imidazoline ring may stimulate insulin secretion independently of alpha(2)-adrenoceptor blockage. Recently, a new ''imidazoline-binding site'' involved in the control of K+-ATP channels in the B cell has been proposed. In the course of searching for new antidiabetic agents, 1-alkyl-2-(4',5'-dihydro-1'H-imidazol-2'-yl)piperazines, 1-benzyl-2-(4',5'-dihydro-1'H-imidazol-2'-yl) and 1-benzyl-2-(4',5'-dihydro-1'H-imidazol-2'-yl)-4-benzylpiperazines have been designed and evaluated as potential adrenoceptor antagonists. Pharmacological evaluation was performed in vivo using glucose tolerance tests performed on a rat model of type II diabetes obtained by injection of a low dose (35 mg/kg) of streptozotocin (STZ). For some compounds, binding experiments were performed on alpha(2) adrenoceptors and I-1 and I-2 imidazoline-binding sites. The biological and physicochemical data have been combined with molecular modeling studies to establish structure-activity relationships. The most active compound was 1-(2',4'-dichlorobenzyl)-2 (4',5'-dihydro-1'H-imidazol-2'-yl)-4-methylpiperazine (7f); intraperitoneal administration (100 mu mol/kg) of 7f strongly improved glucose tolerance in STZ diabetic rats. This effect seemed at least partly mediated by a significant increase of insulin secretion. Other compounds of the same family (7b, 16f, 23b) have also shown potent activity. We found no correlation between in vivo antihyperglycemic properties and in vitro affinities for alpha(2)-adrenoceptors or I-1 and I-2 binding sites. These compounds can be considered as antihyperglycemic agents potentially useful for treatment of type II diabetes and are currently under complementary investigation.

  DOI：

  10.1021/jm9608624

文献信息

• Structure-based design of isoquinoline-5-sulfonamide inhibitors of protein kinase B
  作者：Ian Collins、John Caldwell、Tatiana Fonseca、Alastair Donald、Vassilios Bavetsias、Lisa-Jane K. Hunter、Michelle D. Garrett、Martin G. Rowlands、G. Wynne Aherne、Thomas G. Davies、Valerio Berdini、Steven J. Woodhead、Deborah Davis、Lisa C.A. Seavers、Paul G. Wyatt、Paul Workman、Edward McDonald

  DOI：10.1016/j.bmc.2005.09.055

  日期：2006.2

  Structure-based drug design of novel isoquinoline-5-sulfonamide inhibitors of PKB as potential antitumour agents was investigated. Constrained pyrrolidine analogues that mimicked the bound conformation of linear prototypes were identified and investigated by co-crystal structure determinations with the related protein PKA. Detailed variation in the binding modes between inhibitors with similar overall

  研究了新型PKB异喹啉5磺酰胺抑制剂作为潜在抗肿瘤药的基于结构的药物设计。鉴定并模拟了线性原型的结合构象的约束吡咯烷类似物，并通过与相关蛋白PKA的共晶体结构测定进行了研究。观察到具有相似总体构象的抑制剂之间结合模式的详细变化。该系列中的强效PKB抑制剂在细胞测定中抑制GSK3beta磷酸化，与细胞中PKB激酶活性的抑制一致。
• Aminoheterocyclic derivatives as antithrombotic or anticoagulant
  申请人：Zeneca Limited

  公开号：US05965559A1

  公开（公告）日：1999-10-12

  The invention concerns compounds of formula (I), wherein each of G.sup.1, G.sup.2 and G.sup.6 is CH or n; m is 1 or 2; R.sup.1 includes hydrogen, halogeno and (1-4C)alkyl; M.sup.1 is a group of formula: NR.sup.2 -L.sup.1 -T.sup.1 R.sup.3, in which R.sup.2 and R.sup.3 together form a (1-4C)alkylene group, L.sup.1 includes (1-4C)alkylene, and T.sup.1 is CH or N; A may be a direct link; M.sup.2 is a group of the formula: (T.sup.2 R.sup.4).sub.r -L.sup.2 T.sup.3 R.sup.5 in which R is 0 or 1, each of T.sup.2 and T.sup.3 is CH or N, each of R.sup.4 and R.sup.5 is hydrogen or (1-4C)alkyl, or R.sup.4 and R.sup.5 together form a (1-4C)alkylene group, and L.sup.2 includes (1-4C)alkylene; M.sup.3 may be a direct link to X; X includes sulphonyl; and Q includes naphthyl and a heterocycle moiety; or a pharmaceutically-acceptable salt thereof; processes for their preparation, pharmaceutical compositions containing them and their use as antithrombotic or anticoagulant agents.

  该发明涉及式(I)的化合物，其中G.sup.1、G.sup.2和G.sup.6中的每一个是CH或n；m为1或2；R.sup.1包括氢、卤代和(1-4C)烷基；M.sup.1是式的一个基团：NR.sup.2 -L.sup.1 -T.sup.1 R.sup.3，在其中R.sup.2和R.sup.3共同形成一个(1-4C)烷基基团，L.sup.1包括(1-4C)烷基，T.sup.1为CH或N；A可以是直接连接；M.sup.2是式的一个基团：(T.sup.2 R.sup.4).sub.r -L.sup.2 T.sup.3 R.sup.5，在其中R为0或1，T.sup.2和T.sup.3中的每一个是CH或N，R.sup.4和R.sup.5中的每一个是氢或(1-4C)烷基，或R.sup.4和R.sup.5共同形成一个(1-4C)烷基基团，L.sup.2包括(1-4C)烷基；M.sup.3可以是到X的直接连接；X包括磺酰基；Q包括萘基和杂环基；或其药学上可接受的盐；它们的制备方法，含有它们的药物组合物以及它们作为抗血栓或抗凝血剂的用途。
• Gonadotropin Releasing Hormone Receptor Antagonist, Preparation Method Thereof And Pharmaceutical Composition Comprising The Same
  申请人：Kim Seon Mi

  公开号：US20130137661A1

  公开（公告）日：2013-05-30

  Disclosed are compounds useful as gonadotrophin-releasing hormone (“GnRH”) receptor antagonist.

  披露了作为促性腺激素释放激素（“GnRH”）受体拮抗剂有用的化合物。
• DIHYDROPYRIMIDINE COMPOUNDS AND THEIR APPLICATION IN PHARMACEUTICALS
  申请人：SUNSHINE LAKE PHARMA CO., LTD.

  公开号：US20150152096A1

  公开（公告）日：2015-06-04

  Provided herein are dihydropyrimidine compounds and their pharmaceutical applications, especially for use in treating and preventing HBV diseases. Specifically, provided herein are compounds having Formula (I) or (Ia), or an enantiomer, a diastereoisomer, a tautomer, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof, wherein the variables of the formulas are as defined in the specification. Also provided herein is the use of the compounds having Formula (I) or (Ia), or an enantiomer, a diastereoisomer, a tautomer, a hydrate, a solvate, or a pharmaceutically acceptable salt thereof for treating and preventing HBV diseases.

  本文提供了二氢嘧啶化合物及其药物应用，特别用于治疗和预防HBV疾病。具体来说，本文提供了具有化学式（I）或（Ia）的化合物，或其对映体、二对映异构体、互变异构体、水合物、溶剂合物或其药学上可接受的盐，其中化学式的变量如规范中所定义。本文还提供了利用具有化学式（I）或（Ia）的化合物，或其对映体、二对映异构体、互变异构体、水合物、溶剂合物或其药学上可接受的盐来治疗和预防HBV疾病。
• PIPERAZINE AMIDE DERIVATIVES
  申请人：Dehmlow Henrietta

  公开号：US20090048264A1

  公开（公告）日：2009-02-19

  The invention is concerned with novel piperazine amide derivatives of formula (I) wherein R 1 to R 11 , W, X and Y are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds bind to LXR alpha and LXR beta and can be used as medicaments.

  这项发明涉及一种新型哌嗪酰胺衍生物，其化学式为（I），其中R1至R11、W、X和Y如描述和索赔中定义，并且其生理上可接受的盐。这些化合物能够结合到LXRα和LXRβ，并可用作药物。