ethyl thiazolidine-2-carboxylate | 33305-10-1

• 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: ethyl thiazolidine-2-carboxylate
• 英文别名: thiazolidine-2-carboxylic acid ethyl ester；Thiazolidin-2-carbonsaeure-aethylester；(S)-ethyl thiazolidine-2-carboxylate；(+/-)-Thiazolidin-2-carbonsaeureethylester；2-Ethoxycarbonylthiazolidin；Ethyl 1,3-thiazolidine-2-carboxylate
• CAS: 33305-10-1；65126-73-0；65126-75-2
• 化学式: C₆H₁₁NO₂S
• mdl: MFCD20617278
• 分子量: 161.225
• InChiKey: STIPQAUQYAPPPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

制备方法与用途

乙基噻唑烷-2-甲酸基酯用作研究中的化合物。

反应信息

• 作为反应物：
  描述：

  ethyl thiazolidine-2-carboxylate 生成 (R)-ethyl thiazolidine-2-carboxylate
  参考文献：
  名称：

  Study of the structural requirements for Dopa potentiation and oxotremorine antagonism by L-prolyl-L-leucylglycinamide

  摘要：

  A number of analogs of the tripeptide L-prolyly-L-leucylglycinamide (1) were synthesized and evaluated in the Dopa potentiation and oxotremorine antagonism tests. The replacement of the glycinamide residue with either the glycine methylamide, glycine, aminoacetonitrile, amino-2-propanone, semicarbazide, or beta-alaninamide residues resulted in a loss of activity in both tests. A 1:1 mixture of L-prolyl-L-leucyl-(-)-thiazolidine-2-carboxamide (8) and L-prolyl-L-leucyl-(+)-thiazolidine-2-carboxamide (9) showed marked activity in the Dopa potentiation test but was unable to antagonize the tremors induced by oxotremorine. L-Prolyl-L-leucyl-L-prolinamide (11), on the other hand, was active in the oxotremorine antagonism test but inactive in the Dopa potentiation test. The replacement of the pyrrolidine ring of 1 with either a thiazolidine or cyclopentane ring system caused a loss of activity. The cyclopentanecarboxylic acid analogue 13, however, was found to have moderate activity in the serotonin potentiation test.

  DOI：

  10.1021/jm00200a004
• 作为产物：
  描述：

  (2-amino-ethylsulfanyl)-hydroxy-acetic acid ethyl ester; oxalate (2:1) 生成 ethyl thiazolidine-2-carboxylate
  参考文献：
  名称：

  Fourneau,J.-P. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1971, vol. 272, p. 1515 - 1517

  摘要：

  DOI：

文献信息

• THIAZOLIDINE DERIVATIVES AND METHODS FOR THE PREPARATION THEREOF
  申请人：Kim Sung Soo

  公开号：US20100048570A1

  公开（公告）日：2010-02-25

  The present invention relates to novel 2-carbonyl-3-acyl-1,3-thiazolidines having a β-amino group on the acyl chain, in free, prodrug form or pharmaceutically acceptable salt thereof, including their enantiomers, diastereomers and racemates, as efficient inhibitors against DPP-IV. The invention further relates to the pharmaceutical compositions comprising the disclosed compounds. The present invention also relates to methods for preparing the disclosed compounds and for treating DPP-IV-mediated diseases.

  本发明涉及具有β-氨基团的酰基链上的新型2-羰基-3-酰基-1,3-噻唑啉化合物，包括其自由形式、前药形式或其药用可接受盐，包括它们的对映体、异构体和消旋体，作为高效的DPP-IV抑制剂。该发明还涉及包含所述化合物的药物组合物。本发明还涉及制备所述化合物以及治疗DPP-IV介导的疾病的方法。
• 4-Pyridyl-and 2,4-pyrimidinyl-substituted pyrrole derivatives and their use in pharmacy
  申请人：——

  公开号：US20030153558A1

  公开（公告）日：2003-08-14

  The present invention relates to 4-pyridyl- und 2,4-pyrimidinyl-substituted pyrrole derivatives and their use in pharmacy, of the formula 1 1 in which the variables have the meanings indicated in the description. The compounds according to the invention have immunomodulating and/or cytokine release-inhibiting action and are therefore utilizable for the treatment of disorders which are connected with a disturbance of the immune system.

  本发明涉及4-吡啶基和2,4-嘧啶基取代的吡咯衍生物及其在药学中的应用，其化学式如下所示，其中变量具有描述中指示的含义。根据本发明的化合物具有免疫调节和/或细胞因子释放抑制作用，因此可用于治疗与免疫系统紊乱相关的疾病。
• Discovery of β-aminoacyl containing thiazolidine derivatives as potent and selective dipeptidyl peptidase IV inhibitors
  作者：Woul Seong Park、Seung Kyu Kang、Mi Ae Jun、Mi Sik Shin、Ki Young Kim、Sang Dal Rhee、Myung Ae Bae、Min Sun Kim、Kwang Rok Kim、Nam Sook Kang、Sung-eun Yoo、Jie Oh Lee、Dong Hyun Song、Peter Silinski、Stephen Edward Schneider、Jin Hee Ahn、Sung Soo Kim

  DOI：10.1016/j.bmcl.2011.01.041

  日期：2011.3

  containing thiazolidine derivatives was synthesized and evaluated for their ability to inhibit DPP-IV. Several thiazolidine derivatives with an acid moiety were found to be potent DPP-IV inhibitors. Among them, compound 2da is the most active in this series with an IC50 value of 1 nM, and it showed excellent selectivity over DPP-IV related enzymes including DPP-2, DPP-8, and DPP-9. Compound 2da is chemically

  合成了一系列含有β-氨基酰基的噻唑烷衍生物，并评估了它们抑制DPP-IV的能力。发现具有酸部分的几种噻唑烷衍生物是有效的DPP-IV抑制剂。其中，化合物2da是该系列中活性最高的化合物，IC 50值为1 nM，与DPP-IV相关的酶（包括DPP-2，DPP-8和DPP-9）相比，具有出色的选择性。化合物2da具有化学和代谢稳定性，未显示CYP抑制，hERG结合或细胞毒性。化合物2db（2da的酯类前药）在大鼠和狗模型中口服后显示出良好的体内DPP-IV抑制作用。
• 아다만틸기를 갖는 헤테로고리 카복스아미드 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 약제학적 조성물
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY 한국화학연구원(319980077651)

  公开号：KR20170079939A

  公开（公告）日：2017-07-10

  본 발명은 11β-하이드록시스테로이드 디하이드로게나제 타입 1(11β-hydroxystreroid dehydrogenase type1,11β-HSD1)의 활성을 억제하는 하기 화학식 1로 표시되는 아다만틸기를 갖는 헤테로고리 카복스아미드 유도체, 그의 프로드럭, 그의 용매화물, 그의 입체이성질체 또는 약제학적으로 허용 가능한 그의 염, 이의 제조방법 및 이를 유효성분으로 함유하는 약제학적 조성물에 관한 것이다. [화학식 1] 상기 화학식 1에서, W, X, R, R, L, a 및 b은 발명의 상세한 설명에서 정의한 바와 같다.

  本发明涉及一种含有具有化学式1的阿达曼蒂尔基的杂环羰基衍生物，其抑制11β-羟基类固醇脱氢酶1型（11β-hydroxystreroid dehydrogenase type1, 11β-HSD1）的活性，以及其前药、溶剂化合物、立体异构体或药学上可接受的盐，以及包含其作为有效成分的药学组合物的制备方法。在上述化学式1中，W、X、R、R、L、a和b如本发明的详细描述中定义。
• Synthesis and 11β hydroxysteroid dehydrogenase 1 inhibition of thiazolidine derivatives with an adamantyl group
  作者：Sung Wook Kwon、Seung Kyu Kang、Jae Hong Lee、Joo Hwan Bok、Chi Hyun Kim、Sang Dal Rhee、Won Hoon Jung、Hee Youn Kim、Myung Ae Bae、Jin Sook Song、Duck Chan Ha、Hyae Gyoung Cheon、Ki Young Kim、Jin Hee Ahn

  DOI：10.1016/j.bmcl.2010.10.123

  日期：2011.1

  A new series of thiazolidine derivatives with an adamantyl group was synthesized and evaluated for their ability to inhibit 11β-hydroxysteroid dehydrogenase 1 (11β-HSD1). Our initial compound showed a weak inhibitory activity. Significant improvements in potency were achieved by substituent modification. The potent compound showed good in vitro inhibitory activity toward human 11β-HSD1, selectivity

  合成了一系列新的带有金刚烷基的噻唑烷衍生物，并评估了它们抑制 11β-羟基类固醇脱氢酶 1 (11β-HSD1) 的能力。我们最初的化合物显示出弱的抑制活性。通过取代基修饰实现了效力的显着提高。这种有效的化合物对人 11β-HSD1 表现出良好的体外抑制活性，对 11β-HSD2 具有选择性，代谢稳定性，药代动力学和安全性。此外，该化合物在大鼠和猴子模型中显着抑制 11β-HSD1 活性，并在 KKAy 小鼠中显示出改善的血糖控制。