(R)-3-BOC-噻唑烷基-2-羧酸 | 125471-00-3

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 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: (R)-3-BOC-噻唑烷基-2-羧酸
• 英文名称: (R)-3-(tert-butoxycarbonyl)thiazolidine-2-carboxylic acid
• 英文别名: (2R)-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-thiazolidine-2-carboxylic acid
• CAS: 125471-00-3
• 化学式: C₉H₁₅NO₄S
• 分子量: 233.288
• InChiKey: HYAXPNDMEODKHI-ZCFIWIBFSA-N

物化性质

• 熔点：
  90-93℃
• 沸点：
  385.3±42.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26
• 危险类别码：
  R36/37/38
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  (R)-3-BOC-噻唑烷基-2-羧酸 、 2',3'-异丙叉腺苷 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以77%的产率得到
  参考文献：
  名称：

  Potential utility of adenosine 5′-ester prodrugs to enhance its plasma half-life: synthesis and molecular docking studies

  摘要：

  Adenosine, the adenine nucleoside, has demonstrated various pharmacological properties related to the treatment of relevant clinical diseases. With respect to this, one of the most fascinating biological activities of adenosine is its capacity for reversing hepatic fibrosis, which has been established in several in vitro and in vivo studies. Although adenosine seems to be a privileged compound, it lacks of metabolic stability to be considered as a drug candidate. For this reason, in this preliminary study, six prodrugs were developed in order to enhance the plasma half-life of adenosine, in which the esterification at 5' position of adenosine was considered. According to previous works, the increase in steric hindrance at this position could develop unfavorable interactions inside adenosine deaminase (ADA) catalytic domain, which is reported as the main enzyme implicated in adenosine metabolism. Besides, molecular docking was employed to verify if the hindrance at carbinol group in the prodrugs is enough to diminish its oxidation and also to predict if compounds would be metabolized by a promiscuous esterase. Finally, the in vitro assays corroborated the theoretical findings and also indicated that the compounds are less metabolized than adenosine by ADA; in the case of compounds containing proline and thioproline progroups (4d and 4e, respectively), the reduction was more than three-fold of decrease.

  DOI：

  10.1007/s00044-014-1299-z
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 thiazolidine carboxylic acid 生成 (R)-3-BOC-噻唑烷基-2-羧酸
  参考文献：
  名称：

  Derivatives of 2-(iminomethyl)amino-phenyl, their preparation, their use as medicaments and the pharmaceutical compositions containing them

  摘要：

  从以下化合物组中选择的一种化合物，其化学式为 其中A是从以下组中选择的 其他取代基在规范中定义，具有抑制NO合酶产生一氧化氮的活性和/或捕获活性氧化物种的活性。

  公开号：

  US06335445B1

文献信息

• Discovery and Optimization of Thiazolidinyl and Pyrrolidinyl Derivatives as Inhaled PDE4 Inhibitors for Respiratory Diseases
  作者：Laura Carzaniga、Gabriele Amari、Andrea Rizzi、Carmelida Capaldi、Renato De Fanti、Eleonora Ghidini、Gino Villetti、Chiara Carnini、Nadia Moretto、Fabrizio Facchinetti、Paola Caruso、Gessica Marchini、Loredana Battipaglia、Riccardo Patacchini、Valentina Cenacchi、Roberta Volta、Francesco Amadei、Alice Pappani、Silvia Capacchi、Valentina Bagnacani、Maurizio Delcanale、Paola Puccini、Silvia Catinella、Maurizio Civelli、Elisabetta Armani

  DOI：10.1021/acs.jmedchem.7b01044

  日期：2017.12.28

  identification of novel classes of potent PDE4 inhibitors suitable for pulmonary administration. Starting from a previous series of benzoic acid esters, we explored the chemical space in the solvent-exposed region of the enzyme catalytic binding pocket. Extensive structural modifications led to the discovery of a number of heterocycloalkyl esters as potent in vitro PDE4 inhibitors. (S*,S**)-18e and

  磷酸二酯酶4（PDE4）是一种参与炎症性疾病发病机理的关键cAMP代谢酶，其药理学抑制作用已显示出可在慢性阻塞性肺疾病（COPD）中发挥治疗作用。在本文中，我们描述了一种旨在发现适用于肺部给药的新型新型强效PDE4抑制剂的药物开发程序。从先前的苯甲酸酯系列开始，我们探索了酶催化结合口袋中溶剂暴露区域的化学空间。广泛的结构修饰导致发现许多杂环烷基酯作为有效的体外PDE4抑制剂。（S *，S **）- 18e和（S *，特别地，S **）- 22e在实验动物模型中表现出最佳的体外ADME和药代动力学性质，并剂量依赖性地抵消了急性肺嗜酸性粒细胞增多。最佳的生物学特性以及出色的固态特性表明，这两种化合物都有可能成为治疗呼吸道炎性疾病的有效局部药物。
• N-HYDROXYAMIDE DERIVATIVES POSSESSING ANTIBACTERIAL ACTIVITY
  申请人：Jain Rakesh Kumar

  公开号：US20100022605A1

  公开（公告）日：2010-01-28

  Described herein are N-hydroxyamlde antibacterial compounds, methods for making the compounds, pharmaceutical compositions containing the compounds and methods of treating bacterial infections utilizing the compounds and pharmaceutical compositions compound of Formula (I): or a salt, solvate ti hydrate thereof, wherein A is (a) each indicates a point of attachment.

  本文描述了N-羟基酰胺抗菌化合物，制备这些化合物的方法，含有这些化合物的制药组合物，以及利用这些化合物和制药组合物治疗细菌感染的方法。化合物的化学式如下：或其盐、溶剂合物或水合物，其中A是（a）表示连接点。
• EP2338878A2
  申请人：——

  公开号：EP2338878A2

  公开（公告）日：2011-06-29
• US5250517A
  申请人：——

  公开号：US5250517A

  公开（公告）日：1993-10-05
• US8088804B2
  申请人：——

  公开号：US8088804B2

  公开（公告）日：2012-01-03