(2R,4R)-N-acetyl-2-phenyl-4-carboxy-1,3-thiazolidine | 69739-21-5

• 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: (2R,4R)-N-acetyl-2-phenyl-4-carboxy-1,3-thiazolidine
• 英文别名: (4R)-3-acetyl-2c-phenyl-thiazolidine-4r-carboxylic acid；N-acetyl-N,S-(R)-benzylidene-L-cysteine；(4R)-3-Acetyl-2c-phenyl-thiazolidin-4r-carbonsaeure；(2R,4R)-3-Acetyl-2-phenyl-4-thiazolidinecarboxylic acid；(2R,4R)-3-acetyl-2-phenyl-1,3-thiazolidine-4-carboxylic acid
• CAS: 69739-21-5
• 化学式: C₁₂H₁₃NO₃S
• 分子量: 251.306
• InChiKey: NYATUQLQYZIJCY-WDEREUQCSA-N

物化性质

• 沸点：
  514.1±50.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-萘醌 、 (2R,4R)-N-acetyl-2-phenyl-4-carboxy-1,3-thiazolidine 生成 (R)-5-methyl-3-phenylbenzo[f]thiazolo[4,3-a]isoindole-6,11(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of new naphthoquinone-containing pyrrolo-thiazoles as anticancer agents

  摘要：

  Abstract magnified image Naphthoquinones undergo 1,3‐dipolar cycloaddition with bicyclic münchnones generated from thiazolidines affording new pyrrolo‐thiazoles with a fused quinone nucleus. The products were obtained as single enantiomers in good yields. These benzo[f]thiazolo[4,3‐a]isoindole‐6,11(1H,3H)‐diones are comprised of four fused rings and present a very planar structure. The evaluation of their anticancer activity against melanoma A375 and colorectal adenocarcinoma WiDr human cell lines showed only moderate activity but gave insight into the modeling of new structures. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.] J. Heterocyclic Chem., (2010).

  DOI：

  10.1002/jhet.396
• 作为产物：
  描述：

  L-半胱氨酸 、 乙酸酐 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.67h， 以46%的产率得到(2R,4R)-N-acetyl-2-phenyl-4-carboxy-1,3-thiazolidine
  参考文献：
  名称：

  Kappa-opioid receptor agonist comprising a 2-phenylbenzothiazoline derivative

  摘要：

  公开号：

  EP1496053B1

文献信息

• Synthesis and NMR studies of thiazolidine-4-carboxylic acid derivatives containing a nitro ester function
  作者：Francesca Benedini、Francesco Ferrario、Alberto Sala、Luca Sala、Pier Angelo Soresinetti

  DOI：10.1002/jhet.5570310608

  日期：1994.11

  The preparation of thiazolidine-4-carboxylic acid derivatives containing a 2-nitrooxyethylamine group, potentially active as vasodilators, is reported. Their 1H nmr studies carried out to establish the configuration of the C2 stereocenter and the full assignment of their 1H and 13C nmr spectra, are also reported.

  据报道，含有2-硝基氧乙胺基的噻唑烷-4-羧酸衍生物的制备具有潜在的血管扩张作用。他们还进行了1 H nmr研究，以建立C2立体中心的构型，并完整报道了其1 H和13 C nmr光谱。
• Kappa-opioid receptor agonist comprising 2-phenylbenzothiazoline derivative
  申请人：Tokai Maki

  公开号：US20050113430A1

  公开（公告）日：2005-05-26

  The present invention provides κ opioid receptor agonists comprising 2-phenylbenzothiazoline derivatives. The present invention relates to κ opioid receptor agonists comprising compounds or salts thereof having the chemical structure represented by the general formula [I]. Namely, it is important for exhibition of the κ opioid receptor agonist actions to have an alkyl group having an amino group at a phenyl group of 2-phenylbenzothiazoline as a substituent and to have an acyl group at a nitrogen atom of 2-phenylbenzothiazoline, wherein R is alkyl having the amino group as the substituent; and R 1 is acyl.

  本发明提供了包含2-苯基苯并噻唑衍生物的κ阿片受体激动剂。本发明涉及化学结构式[I]所表示的化合物或其盐，其包含κ阿片受体激动剂，即在2-苯基苯并噻唑的苯基上具有氨基取代基的烷基取代基，并在2-苯基苯并噻唑的氮原子上具有酰基取代基，这对于展示κ阿片受体激动剂作用非常重要，其中R是具有氨基取代基的烷基取代基；R1是酰基。
• Method for treating pain or pruritis by administering opinoid receptor agonist comprising 2-phenylbenzothiazoling derivative
  申请人：Tokai Maki

  公开号：US20060205796A1

  公开（公告）日：2006-09-14

  A method of treating pain or pruritis comprising administering to a patient in need thereof a pharmaceutically effective amount of a κ opioid receptor agonist of the formula wherein R is an alkyl having an amino group as a substituent; and R 1 is acyl.

  一种治疗疼痛或瘙痒的方法，包括向需要治疗的患者给予药效有效量的κ阿片受体激动剂，该激动剂的化学式为其中R是具有氨基基团的烷基；R1是酰基。
• KAPPA-OPIOID RECEPTOR AGONIST COMPRISING 2-PHENYLBENZOTHIAZOLINE DERIVATIVE
  申请人：SANTEN PHARMACEUTICAL CO., LTD.

  公开号：EP1496053A1

  公开（公告）日：2005-01-12

  The present invention provides κ opioid receptor agonists comprising 2-phenylbenzothiazoline derivatives. The present invention relates to κ opioid receptor agonists comprising compounds or salts thereof having the chemical structure represented by the general formula [I]. Namely, it is important for exhibition of the κ opioid receptor agonist actions to have an alkyl group having an amino group at a phenyl group of 2-phenylbenzothiazoline as a substituent and to have an acyl group at a nitrogen atom of 2-phenylbenzothiazoline, wherein R is alkyl having the amino group as the substituent; and R1 is acyl.

  本发明提供了由 2-苯基苯并噻唑啉衍生物组成的 κ 阿片受体激动剂。本发明涉及由具有通式[I]所代表的化学结构的化合物或其盐组成的κ阿片受体激动剂。也就是说，对于展示κ阿片受体激动剂的作用而言，重要的是在 2-苯基苯并噻唑啉的苯基上具有氨基的烷基作为取代基，并且在 2-苯基苯并噻唑啉的氮原子上具有酰基、 其中 R 是以氨基为取代基的烷基；R1 是酰基。
• Heterocyclische Verbindungen aus Zuckern, XV: Zur Konfiguration chiraler C-2-substituierter 4-Thiazolidincarbons�uren. Chiralit�tstransfer auf C-3 in 3,4-Dihydro-1H-pyrrolo[1,2-c]thiazolen
  作者：Z. Gy�rgyde�k、L. Szil�gyi、J. Kajt�r、G. Argay、A. K�lm�n

  DOI：10.1007/bf00818164

  日期：1994.2

  5-Substituted 3,4-dihydro-pyrrolo[1,2-c]thiazole-6,7-dicarboxylic acid esters 3 are obtained from 2-substituted-3-acyl-1,3-thiazolidine-4-carboxylic acids, 1 in [3 + 2]-cycloaddition reactions via mesoionic oxazolone (''munchnone'') intermediates. The chirality at C-4 of the starting carboxylic acids 1 is eliminated in the products 3, and the chirality at C-3 (C-2 in the starting carboxylic acids 1) can thus be determined through chiroptical measurements. Several representatives of the ring system 3 have been characterised through H-1- and CD-spectra and the molecular structure of (3S)-3da has been determined by X-ray crystallography.