L-噻唑烷-4-羧酸 | 45521-09-3

• 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: L-噻唑烷-4-羧酸
• 中文别名: D-噻莫西酸；D-硫代脯氨酸；D-噻唑啉甲酸；D-噻唑烷酸；D-1,3-噻唑啉-4-甲酸；D-硫杂脯氨酸
• 英文名称: L-thiaproline
• 英文别名: (S)-thiazolidine-4-carboxylic acid；L-4-thiazolidinecarboxylic acid；thioproline；L-(-)-thiazolidine-4-carboxylic acid；D-thiazolidine-4-carboxylic acid；D-4-thiazolidinecarboxylic acid；(4S)-1,3-thiazolidin-3-ium-4-carboxylate
• CAS: 45521-09-3
• 化学式: C₄H₇NO₂S
• mdl: MFCD00063637
• 分子量: 133.171
• InChiKey: DZLNHFMRPBPULJ-GSVOUGTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P310+P330,P302+P352+P312,P304+P340+P312,P305+P351+P338,P332+P313,P337+P313,P403+P233,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301,H312+H332,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避光保存，并需置于惰性气体环境中。

反应信息

• 作为反应物：
  描述：

  L-噻唑烷-4-羧酸 生成 D-半胱氨酸
  参考文献：
  名称：

  SHIRAIWA, TADASHI;KATAOKA, KAZUO;SAKATA, SHINJI;KUROKAWA, HIDEMOTO, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 109-113

  摘要：

  DOI：
• 作为产物：
  描述：

  噻莫西酸 以0.290 g的产率得到L-噻唑烷-4-羧酸
  参考文献：
  名称：

  用 L-氨基酸代替 (RS)-4-噻唑烷羧酸的结晶作为共溶质进行光学拆分

  摘要：

  通过替换 (RS)-4-噻唑烷羧酸 [(RS)-THC] 的结晶进行光学拆分与共存的 8 个 L-氨基酸进行，并检查后者的影响。L-异亮氨酸 [L-Ile] 和 L-半胱氨酸 [L-Cys] 作为共溶质导致 (R)-THC 从 (RS)-THC 的水溶液中优先结晶，而其他 L-氨基酸产生 ( S)-四氢大麻酚。L-Cys、L-苏氨酸、L-4-羟脯氨酸 [L-Hyp] 和 L-丝氨酸作为共溶质似乎比 L-Ile、L-缬氨酸、L-脯氨酸和 L-Ile 对一种对映体的结晶具有更好的选择性L-丙氨酸。成功实现了 L-Hyp 的光学拆分，并提出了连续光学拆分的可能性，以提供 (R)- 和 (S)-THC。

  DOI：

  10.1246/bcsj.65.267

文献信息

• Synthesis of Functionalized 3-Spiro[cyclopropa[<i>a</i>]pyrrolizine]- and 3-Spiro[3-azabicyclo[3.1.0]hexane]oxindoles from Cyclopropenes and Azomethine Ylides via [3 + 2]-Cycloaddition
  作者：Alexander S. Filatov、Nickolay A. Knyazev、Alexander P. Molchanov、Taras L. Panikorovsky、Rafael R. Kostikov、Anna G. Larina、Vitali M. Boitsov、Alexander V. Stepakov

  DOI：10.1021/acs.joc.6b02505

  日期：2017.1.20

  substituted isatins, α-amino acids, and cyclopropenes. The key step is an intramolecular [3 + 2]-cycloaddition reaction of an in situ generated azomethine ylide onto a cyclopropene. Both N-substituted and N-unsubstituted α-amino acids, dipeptide Gly-Gly, and also benzylamine were used as the amine component for the azomethine ylide generation. The anticancer activity of some of the obtained compounds

  使用取代的靛红，α-氨基酸通过一锅式三组分反应以中等至高收率制备3-螺[环丙[ a ]吡咯嗪]-和3-螺[3-氮杂双环[3.1.0]己烷]氧吲哚和环丙烯。关键步骤是将原位生成的甲亚胺叶立德分子与环丙烯进行分子内[3 + 2]环加成反应。既Ñ取代和ñ -未被取代的α氨基酸，二肽甘氨酸-甘氨酸，并且还苄胺用作偶氮甲碱内鎓盐生成的胺组分。的一些针对人白血病K562细胞系中获得的化合物的抗癌活性，通过流式细胞术评估体外。
• [EN] NOVEL DIPEPTIDYL PEPTIDASE IV INHIBITORS; PROCESSES FOR THEIR PREPARATION AND COMPOSITIONS THEREOF<br/>[FR] NOUVEAUX INHIBITEURS DE DIPEPTIDYLE PEPTIDASE IV, LEUR PROCEDES DE PREPARATION ET COMPOSITIONS EN COMPORTANT
  申请人：GLENMARK PHARMACEUTICALS LTD

  公开号：WO2005075426A1

  公开（公告）日：2005-08-18

  The present invention relates to novel dipeptidyl peptidase IV (DPP-IV) inhibitors or general formula (1) useful for treating diabetes, non-insulin dependent diabetes mellitus, impaired glucose tolerance, inflammatory bowel disease, ulcerative colitis,Chron’s disease, obesity, and metabolic syndrome.

  本发明涉及一种新型二肽基肽酶IV（DPP-IV）抑制剂，其一般式（1）用于治疗糖尿病、非胰岛素依赖型糖尿病、糖耐量受损、炎症性肠病、溃疡性结肠炎、克罗恩病、肥胖症和代谢综合征。
• Inhibitors of &agr;4&bgr;1 mediated cell adhesion
  申请人：Pharmacia & Upjohn Company

  公开号：US06685617B1

  公开（公告）日：2004-02-03

  The present invention relates to compound of formula (I), that are potent inhibitors of &agr;4&bgr;1 mediated adhesion to either VCAM or CS-1 and which could be useful for the treatment of inflammatory diseases. Specifically, the molecules of the present invention can be used for treating or preventing &agr;4&bgr;1 adhesion mediated conditions in a mammal such as a human. This method may comprise administering to a mammal or a human patient an effective amount of the compound or composition as explained in the present specification.

  本发明涉及式(I)的化合物，它们是α4β1介导的对VCAM或CS-1的黏附的有效抑制剂，可用于治疗炎症性疾病。具体来说，本发明的分子可用于治疗或预防哺乳动物，如人类，中的α4β1介导的黏附状况。该方法可能包括向哺乳动物或人类患者施用本说明书中所述的化合物或组合物的有效量。
• Characterization of amino acid-derived betaines by electrospray ionization tandem mass spectrometry
  作者：V. Naresh Chary、Ch. Dinesh Kumar、M. Vairamani、S. Prabhakar

  DOI：10.1002/jms.2029

  日期：2012.1

  Betaines belong to the naturally occurring osmoprotectants or compatible solutes present in a variety of plants, animals and microorganisms. In recent years, metabolomic techniques have been emerging as a fundamental tool for biologists because the constellation of these molecules and their relative proportions provide with information about the actual biochemical condition of a biological system. Therefore, identification and characterization of biologically important betaines are crucial, especially for metabolomic studies. Most of the natural betaines are derived from amino acids and related homologues. Although, theoretically, all the amino acids can be converted to corresponding betaines by simple methylation of the amine group, only a few of the amino acid-derived betaines were fully characterized in the literature. Here, we report a combined electrospray ionization tandem and high-resolution mass spectrometry study of all the betaines derived from amino acids, including the isomeric betaines. The decomposition pathway of protonated, sodiated and potassiated molecule ions that enable unambiguous characterization of the betaines including the isomeric betaines and overlapping ionic species of different betaines is distinctive. Copyright © 2012 John Wiley & Sons, Ltd.

  甜菜碱属于自然界中存在的渗透保护剂或相容性溶质，存在于各种植物、动物和微生物中。近年来，代谢组学技术已成为生物学家的基本工具，因为这些分子及其相对比例的组合提供了有关生物系统实际生化状态的信息。因此，鉴定和表征生物学上重要的甜菜碱至关重要，特别是对于代谢组学研究。大多数天然甜菜碱来源于氨基酸及其相关同源物。理论上，所有氨基酸都可以通过氨基的简单甲基化转化为相应的甜菜碱，但文献中只有少数几种氨基酸衍生甜菜碱被完全表征。在这里，我们报道了一种综合电喷雾电离串联和高分辨率质谱研究，研究了所有氨基酸衍生的甜菜碱，包括异构甜菜碱。质子化、钠化和钾化的分子离子的分解途径可以对甜菜碱进行明确表征，包括异构甜菜碱和不同甜菜碱的重叠离子物种。版权所有 © 2012 John Wiley & Sons, Ltd.
• Synthesis and Biological Activity of Novel L-Amino Acid Based Analgesic Compounds
  作者：Junzhu Pan、Qianqian Wang、Gu He、Liang Ouyang、Li Guo

  DOI：10.2174/157018010791163497

  日期：2010.6.1

  Synthesis and analgesic activity studies of a series of L-amino acid based compounds were described. These compounds were designed as potential N-type Calcium Channel Blockers and their structures were confirmed by 1H NMR and ESI-MS spectra. Some of the compounds exhibited significant analgesic activity in Mouse Hot-Plate tests. According to the data of pharmacological experiments, we carried out preliminary

  描述了一系列基于L-氨基酸的化合物的合成和镇痛活性。这些化合物被设计为潜在的N型钙通道阻滞剂，其结构通过1H NMR和ESI-MS光谱确认。某些化合物在Mouse Hot-Plate测试中显示出明显的镇痛活性。根据药理实验数据，我们进行了初步的结构活性研究，结果表明这种化合物可用于开发新的止痛药。