Cyclobutanecarboxylic acid, 1-amino-3-(hydroxymethyl)-, trans- (9CI) | 116823-32-6

• 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: Cyclobutanecarboxylic acid, 1-amino-3-(hydroxymethyl)-, trans- (9CI)
• 英文别名: trans-1-amino-3-(hydroxymethyl)cyclobutane-1-carboxylic acid
• CAS: 116823-32-6
• 化学式: C₆H₁₁NO₃
• 分子量: 145.158
• InChiKey: URCBHRLIPUAWTF-DTXYKFKXSA-N

物化性质

• 沸点：
  326.2±17.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  10.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  83.55
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 Cyclobutanecarboxylic acid, 1-amino-3-(hydroxymethyl)-, trans- (9CI) 在 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 以79%的产率得到
  参考文献：
  名称：

  1-Aminocyclobutanecarboxylic Acid Derivatives as Novel Structural Elements in Bioactive Peptides:  Application to Tuftsin Analogs

  摘要：

  Four novel 2,4-methano amino acids (MAAs, 1-aminocyclobutane-1-carboxylic acids) were synthesized. These include the basic MAA analogs of lysine (16), ornithine (5), and arginine (6) and the neutral methanovaline (22), related to proline. The above MAAs, as well as the MAA analog of homothreonine (7), were incorporated into the peptide chain of the immuno-modulatory peptide tuftsin, Thr-Lys-Pro-Arg, known to enhance several biological activities mediated by phagocytic cells. The synthetic methano tuftsin analogs were assayed for their ability to stimulate interleukin-6 (IL-6) secretion by mouse peritoneal macrophages and for their stability in human serum toward enzymatic degradation. It was found that, at 2 x 10(-7) M, [MThr(1)]tuftsin (24) and an isomer of [MVal(3)]tuftsin (27a) were considerably more active than the parent peptide in augmentation of cytokine release. [MOrn(2)]Tuftsin (25) was equally potent. The analogs [MThr(1)]tuftsin (24) and [MOrn(2)]tuftsin (25), both pertaining to the proteolytically sensitive Thr-Lys bond of tuftsin, exhibited high resistance to enzymatic hydrolysis as compared to tuftsin. Using specific rabbit anti-tuftsin antibodies in a competitive enzyme-linked immunosorbent assay (ELISA) revealed that none of the MAA analogs can crossreact with tuftsin. It may indicate that the peptides assume global structures different than that of tuftsin.

  DOI：

  10.1021/jm960390t
• 作为产物：
  描述：

  3-oxabicyclo<3.1.1>heptan-2-one-1-carboxylic acid 在 盐酸 、 sodium azide 作用下， 以 丙酮 为溶剂， 反应 8.0h， 生成 Cyclobutanecarboxylic acid, 1-amino-3-(hydroxymethyl)-, trans- (9CI)
  参考文献：
  名称：

  顺式和反式-1-氨基-3-羟甲基-环丁烷-1-羧酸的合成

  摘要：

  描述了由3-氧杂双环[3.1.1]庚烷-2-酮-1-羧酸从顺式和反式1-氨基-3-羟甲基-环丁烷-1-羧酸的立体有择合成。

  DOI：

  10.1016/s0040-4020(01)90351-5

文献信息

• [EN] 1,3,4-OXADIAZOLE-2-CYCLOBUTYL COMPOUNDS, PREPARATION METHOD THEREFOR AND APPLICATION THEREOF<br/>[FR] COMPOSÉS DE 1,3,4-OXADIAZOLE-2-CYCLOBUTYL, PROCÉDÉ DE PRÉPARATION CORRESPONDANT ET UTILISATION ASSOCIÉE<br/>[ZH] 1,3,4-噁二唑-2-环丁基类化合物及其制备方法和应用
  申请人：NANJING SANHOME PHARMACEUTICAL CO LTD

  公开号：WO2020083336A1

  公开（公告）日：2020-04-30

  本发明属于医药化学领域，涉及一类1,3,4-噁二唑-2-环丁基类化合物或其药学可接受的盐、水合物、溶剂合物或结晶及它们的制备方法和应用。具体地，本发明提供式(I)的(((1r,3S)-1-(5-((1S,2R)-1-氨基-2-羟丙基)-1,3,4-噁二唑-2-基)-3-(氰甲基)环丁基)氨基甲酰基)-L-丝氨酸或其药学可接受的盐、水合物、溶剂合物或结晶及它们的制备方法和治疗癌症或者感染类疾病的应用， (I).
• Gaoni, Yehiel, Organic Preparations and Procedures International, 1995, vol. 27, # 2, p. 185 - 212
  作者：Gaoni, Yehiel

  DOI：——

  日期：——