(2S)-2-piperidinecarboxylic acid L-tartrate | 15912-30-8

• 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
• 英文名称: (2S)-2-piperidinecarboxylic acid L-tartrate
• 英文别名: L-pipecolic acid l-tartrate；2,3-dihydroxybutanedioic acid;(2S)-piperidine-2-carboxylic acid
• CAS: 15912-30-8；35677-82-8；98626-57-4；109731-18-2；111478-73-0；112797-03-2；128684-94-6；138804-98-5
• 化学式: C₄H₆O₆*C₆H₁₁NO₂
• 分子量: 279.247
• InChiKey: DPNBCUQPARXJAN-JEDNCBNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.91
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  164
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S)-2-piperidinecarboxylic acid L-tartrate 在 Amberlite IR-120 作用下， 以 水 为溶剂， 以59%的产率得到L-哌啶-2-甲酸
  参考文献：
  名称：

  Synthesis of 2-piperidinecarboxylic acid derivatives as potential anticonvulsants

  摘要：

  A variety of 2-piperidinecarboxamides were synthesized and evaluated for anticonvulsant activity using the MES and sc PTZ tests in mice and rats. Neurotoxicity was determined by the rotorod test. Several N-(benzyl)-2-piperidinecarboxamides exhibited potent MES activity in mice [2-CF3 14, ED50 = 29 mg/kg; 3-F 16, ED50 = 31 mg/kg; and 3-CF3 17, ED50 = 24 mg/kg]. The most active compounds in the MES test in mice were the 2,6-dimethylanilides [(R,S)-34, ED50 = 5.8 mg/kg; (R)-35, ED50 = 5.7 mg/kg; and (S)-36, ED50 = 14.8 mg/kg]. The enantiomer (S)-36 was about two-fold less potent in the MES test than (R)-35 and also was less neurotoxic. Acylation of the piperidine ring nitrogen of 12 and 34 led to a decrease in the MES activity. In the N-(alpha-methylbenzyl)-2-piperidine-carboxamides, the stereochemistry at either the 2-position of the piperidine ring or at the alpha-position of the N-(alpha-methylbenzyl) group does not significantly affect MES activity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80072-5
• 作为产物：
  描述：

  D-酒石酸 、 六氢吡啶-alpha-羧酸 以 甲醇 为溶剂， 以75%的产率得到(2S)-2-piperidinecarboxylic acid L-tartrate
  参考文献：
  名称：

  Synthesis of 2-piperidinecarboxylic acid derivatives as potential anticonvulsants

  摘要：

  A variety of 2-piperidinecarboxamides were synthesized and evaluated for anticonvulsant activity using the MES and sc PTZ tests in mice and rats. Neurotoxicity was determined by the rotorod test. Several N-(benzyl)-2-piperidinecarboxamides exhibited potent MES activity in mice [2-CF3 14, ED50 = 29 mg/kg; 3-F 16, ED50 = 31 mg/kg; and 3-CF3 17, ED50 = 24 mg/kg]. The most active compounds in the MES test in mice were the 2,6-dimethylanilides [(R,S)-34, ED50 = 5.8 mg/kg; (R)-35, ED50 = 5.7 mg/kg; and (S)-36, ED50 = 14.8 mg/kg]. The enantiomer (S)-36 was about two-fold less potent in the MES test than (R)-35 and also was less neurotoxic. Acylation of the piperidine ring nitrogen of 12 and 34 led to a decrease in the MES activity. In the N-(alpha-methylbenzyl)-2-piperidine-carboxamides, the stereochemistry at either the 2-position of the piperidine ring or at the alpha-position of the N-(alpha-methylbenzyl) group does not significantly affect MES activity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80072-5

文献信息

• Heterocyclic compounds as inhibitors of rotomase enzymes
  申请人：Pfizer Inc.

  公开号：US06610707B1

  公开（公告）日：2003-08-26

  Compounds of the formula: wherein R1, Y, W, A and R2 are as defined above are inhibitors of rotamase enzymes in particular FKBP-12 and FKBP-52. The compounds therefore moderate neuronal regeneration and outgrowth and can be used for treating neurological disorders arising from neurodegenerative diseases and nerve damage.

  该式化合物：其中R1、Y、W、A和R2如上所定义，是特定的FKBP-12和FKBP-52的旋转酶酶抑制剂。因此，这些化合物可以调节神经再生和生长，并可用于治疗由神经退行性疾病和神经损伤引起的神经系统疾病。
• Synthesis of thyrotropin-releasing hormone analogs with selective central nervous system effects
  作者：Ruth F. Nutt、Frederick W. Holly、Carl Homnick、Ralph Hirschmann、Daniel F. Veber、Byron H. Arison

  DOI：10.1021/jm00138a010

  日期：1981.6

  Thyrotropin-releasing hormone (TRH) analogues which show relative selectivity for action in the central nervous system have been recognized. Practical syntheses for three of these TRH analogues which show the greatest selectivity, less than Aad-His-Tzl-NH2 (5), less than Glu-His-Pip-OMe (2), and less than Aad-His-Pro-NH2 (6), are described. The first two were prepared by solution methods of peptide

  促甲状腺激素释放激素（TRH）类似物在中枢神经系统中显示出相对的选择性。三种TRH类似物的实用合成物显示出最高的选择性，低于Aad-His-Tzl-NH2（5），低于Glu-His-Pip-OMe（2）和低于Aad-His-Pro-NH2 （6），有描述。前两种是通过肽合成的溶液方法制备的。通过固相方法制备化合物6。为了获得最佳收率，组氨酸外消旋化，容易的二酮哌嗪形成和酰化的噻唑烷羧酸衍生物在酸性条件下的不稳定性问题已被最小化。已检查了诸如pK，NMR位移和圆二色性等物理性质，因为它们可能与生物学活性和肽构象有关。
• Use of N-Fmoc amino acid chlorides and activated 2-(fluorenylmethoxy)-5(4H)-oxazolones in solid-phase peptide synthesis. Efficient syntheses of highly N-alkylated cyclic hexapeptide oxytocin antagonists related to L-365,209
  作者：Debra S. Perlow、Jill M. Erb、Norman P. Gould、Roger D. Tung、Roger M. Freidinger、Peter D. Williams、Daniel F. Veber

  DOI：10.1021/jo00042a016

  日期：1992.7

  Fmoc amino acid chlorides have been shown to be useful reagents in the solid-phase synthesis of hexapeptides containing up to four sequential secondary amino acids. The oxytocin antagonist cyclo-(D-Phe-Ile-D-Pip-Pip-D-(N-Me)Phe-Pro) (1) was prepared in 70% overall yield starting from Boc-L-Pro-O-(PAM)-resin. In the synthesis of 1, the high reactivity of Fmoc-L-pipecolic acid chloride used in the di- to tripeptide step averted diketopiperazine formation seen with active ester couplings. The use of Fmoc-amino acid chlorides in the subsequent couplings provided a rapid method for assembly of the linear hexapeptide. The two potent cyclic hexapeptide oxytocin antagonists L-366,682 and L-366,948 were prepared in 45-48% overall yield on a 20 mmol scale using the methodology developed for the synthesis of 1. A particularly difficult coupling was encountered that involved acylation of a sterically hindered N(delta)-Cbz-piperazic acid N-terminus with Fmoc-L-isoleucine. Excess Fmoc-L-isoleucine acid chloride in the presence of tertiary amine base gave only 30% conversion. The efficiency was improved to 76% by utilizing the acid chloride with AgCN in toluene. Further investigation revealed that this combination of reagents produces an activated form of the isoleucine 2-alkoxy-5(4H)-oxazolone derivative.
• HETEROCYCLIC COMPOUNDS AS INHIBITORS OF ROTAMASE ENZYMES
  申请人：PFIZER INC.

  公开号：EP1060178A1

  公开（公告）日：2000-12-20
• US6610707B1
  申请人：——

  公开号：US6610707B1

  公开（公告）日：2003-08-26