2-(1-乙酰基哌啶-3-基)乙酸 | 169253-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 2-(1-乙酰基哌啶-3-基)乙酸
• 英文名称: 1-N-ACETYL-3-PIPERIDINYLACETIC ACID
• 英文别名: 1-Acetyl-3-piperidineacetic Acid；2-(1-acetylpiperidin-3-yl)acetic acid
• CAS: 169253-07-0
• 化学式: C₉H₁₅NO₃
• 分子量: 185.223
• InChiKey: UHQRCEZHYXCOPY-UHFFFAOYSA-N

物化性质

• 沸点：
  389.6±15.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-乙酰基哌啶-3-基)乙酸 在 N-羟基-7-氮杂苯并三氮唑 、 三乙酰氧基硼氢化钠 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 2-(1-acetylpiperidin-3-yl)-N-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-spiro[indene-1,4'-piperidine]-1'-ylbutanamide
  参考文献：
  名称：

  4-Amino-2-alkyl-butyramides as small molecule CCR2 antagonists with favorable pharmacokinetic properties

  摘要：

  A systematic examination of the central aromatic portion of the lead (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-(4-fluorophenyl)-4-(1'H-spiro[indene-1,4'-piperidin]-1'-yl)butanamide (9) led to the discovery of a novel class of CCR2 receptor antagonists, which carry small alicyclic groups such as cyclopropyl, cylobutyl, or cyclopropylmethyl attached at C-2 of the carbon backbone. The most potent compound discovered, namely (2S)-N-[3,5-bis(trifluoromethyl)benzyl]-2-cyclopropyl-4-[(1R,3'R)-3'-methyl-1'H-spiro[indene-1,4'-piperidin]-1'-yl]butanamide (29), showed very high binding affinity (IC50 = 4 nM, human monocyte) and excellent selectivity toward other related chemokine receptors. The excellent pharmacokinetic profile of this new lead compound allows for extensive in vivo evaluation. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.011
• 作为产物：
  描述：

  3-哌啶乙酸 在 乙酸酐 作用下， 以 甲醇 为溶剂， 生成 2-(1-乙酰基哌啶-3-基)乙酸
  参考文献：
  名称：

  Tricyclic amide and urea compounds useful for inhibition of g-protein

  摘要：

  抑制Ras功能从而抑制细胞异常生长的方法已被披露。该方法包括向生物系统中施用Formula 1.0的化合物：##STR1##。具体来说，该方法抑制了哺乳动物（如人类）中细胞的异常生长。还披露了Formula 5.0、5.1和5.2的新化合物，其中R为--C(R.sup.20)(R.sup.21)(R.sup.46)，以及Formula 5.3、5.3A和5.3B，其中R为--N(R.sup.25)(R.sup.48)。还披露了制备Formula 5.0、5.1、5.2和5.3的3-取代化合物的方法。此外，还披露了在制备Formula 5.0、5.1、5.2和5.3的3-取代化合物过程中的中间体新化合物。

  公开号：

  US05719148A1

文献信息

• Tricyclic compounds useful for inhibition of G-protein function and for
  申请人：Schering Corporation

  公开号：US05672611A1

  公开（公告）日：1997-09-30

  Novel compounds of Formula ##STR1## are disclosed. Also disclosed is a method of inhibiting Ras function and therefore inhibiting the abnormal growth of cells. The method comprises administering a compound of the Formula 1.0 to a biological system. In particular, the method inhibits the abnormal growth of cells in a mammal such as a human being.

  揭示了化学式##STR1##的新化合物。还揭示了一种抑制Ras功能从而抑制细胞异常生长的方法。该方法包括向生物系统施用化合物1.0的步骤。具体来说，该方法抑制了哺乳动物（如人类）中细胞的异常生长。
• Tricyclic amide and urea compounds useful for inhibition of g-protein
  申请人：Schering Corporation

  公开号：US05719148A1

  公开（公告）日：1998-02-17

  A method of inhibiting Ras function and therefore inhibiting the abnormal growth of cells is disclosed. The method comprises the administration of a compound of Formula 1.0: ##STR1## to a biological system. In particular, the method inhibits the abnormal growth of cells in a mammal such as a human being. Novel compounds of formulas 5.0, 5.1 and 5.2, wherein R is --C(R.sup.20)(R.sup.21)(R.sup.46), and 5.3, 5.3A and 5.3B, wherein R is --N(R.sup.25)(R.sup.48), are disclosed. Also disclosed are processes for making 3-substituted compounds of Formulas 5.0, 5.1, 5.2 and 5.3. Further disclosed are novel compounds which are intermediates in the process for making 3-substituted compounds of Formulas 5.0, 5.1, 5.2 and 5.3.

  抑制Ras功能从而抑制细胞异常生长的方法已被披露。该方法包括向生物系统中施用Formula 1.0的化合物：##STR1##。具体来说，该方法抑制了哺乳动物（如人类）中细胞的异常生长。还披露了Formula 5.0、5.1和5.2的新化合物，其中R为--C(R.sup.20)(R.sup.21)(R.sup.46)，以及Formula 5.3、5.3A和5.3B，其中R为--N(R.sup.25)(R.sup.48)。还披露了制备Formula 5.0、5.1、5.2和5.3的3-取代化合物的方法。此外，还披露了在制备Formula 5.0、5.1、5.2和5.3的3-取代化合物过程中的中间体新化合物。
• Tricyclic amide and urea compounds useful for inhibition of G-protein function and for treatment of proliferative diseases
  申请人：——

  公开号：US20020068742A1

  公开（公告）日：2002-06-06

  A method of inhibiting Ras function and therefore inhibiting the abnormal growth of cells is disclosed. The method comprises the administration of a compound of Formula 1.0: 1 to a biological system. In particular, the method inhibits the abnormal growth of cells in a mammal such as a human being. Novel compounds of the formulas 2 are disclosed. Also disclosed are processes for making 3-substituted compounds of Formulas 5.0, 5.1, 5.2 and 5.3. Further disclosed are novel compounds which are intermediates in the process for making 3-substituted compounds of Formulas 5.0, 5.1, 5.2 and 5.3.

  本发明揭示了一种抑制Ras功能，从而抑制细胞异常生长的方法。该方法包括向生物系统中给予1.0:1化合物的管理。特别是，在哺乳动物如人类中，该方法抑制细胞异常生长。还揭示了公式2的新化合物。还揭示了制备公式5.0、5.1、5.2和5.3的3-取代化合物的过程。此外，还揭示了在制备公式5.0、5.1、5.2和5.3的3-取代化合物的过程中的新化合物，这些新化合物是中间体。
• Inhibitors of Farnesyl Protein Transferase. 4-Amido, 4-Carbamoyl, and 4-Carboxamido Derivatives of 1-(8-Chloro-6,11-dihydro-5<i>H</i>-benzo[5,6]- cyclohepta[1,2-<i>b</i>]pyridin-11-yl)piperazine and 1-(3-Bromo-8-chloro-6,11- dihydro-5<i>H</i>-benzo[5,6]cyclohepta[1,2-<i>b</i>]pyridin-11-yl)piperazine
  作者：Alan K. Mallams、Randall R. Rossman、Ronald J. Doll、Viyyoor M. Girijavallabhan、Ashit K. Ganguly、Joanne Petrin、Lynn Wang、Robert Patton、W. Robert Bishop、Donna M. Carr、Paul Kirschmeier、Joseph J. Catino、Matthew S. Bryant、Kwang-Jong Chen、Walter A. Korfmacher、Cymbelene Nardo、Shiyong Wang、Amin A. Nomeir、Chin-Chung Lin、Zujun Li、Jianping Chen、Suining Lee、Janet Dell、Philip Lipari、Michael Malkowski、Bodan Yaremko、Ivan King、Ming Liu

  DOI：10.1021/jm970462w

  日期：1998.3.1

  The synthesis of a variety of novel 4-amido, 4-carbamoyl and 4-carboxamido derivatives of 1-(8-chloro-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin -11-yl)piperazine to explore the SAR of of this series of FPT inhibitors is described. This resulted in the synthesis of the 4- and 3-pyridylacetyl analogues 45a and 50a, respectively, both of which were orally active but were found to be rapidly metabolized in vivo. Identification of the principal metabolites led to the synthesis of a variety of new compounds that would be less readily metabolized, the most interesting of which were the 3- and 4-pyridylacetyl N-oxides 80a and 83a. Novel replacements for the pyridylacetyl moiety were also sought, and this resulted in the discovery of the 4-N-methyl and 4-N-carboxamidopiperidinylacetyl derivatives 135a and 160a, respectively. All of these derivatives exhibited greatly improved pharmacokinetics. The synthesis of the corresponding 3-bromo analogues resulted in the discovery of the 4-pyridylacetyl N-oxides 83b (+/-) and 85b [11S(-)] and the 4-carboxamidopiperidinylacetamido derivative 160b (+/-), all of which exhibited potent FPT inhibition in vitro. All three showed excellent oral bioavailability in vivo in nude mice and cynomolgus monkeys and exhibited excellent antitumor efficacy against a series of tumor cell lines when dosed orally in nude mice.
• US6242458B1
  申请人：——

  公开号：US6242458B1

  公开（公告）日：2001-06-05