(-)-(2S,4S)-3-acetyl-5,5-dimethyl-2-phenyl-4-thiazolidinecarboxylic acid | 79913-44-3

• 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
• 英文名称: (-)-(2S,4S)-3-acetyl-5,5-dimethyl-2-phenyl-4-thiazolidinecarboxylic acid
• 英文别名: 3-acetyl-2(S)-phenyl-5,5-dimethylthiazolidine-4(S)-carboxylic acid；(2S,4S)-3-acetyl-5,5-dimethyl-2-phenyl-4-thiazolidinecarboxylic acid；3-Acetyl-5,5-dimethyl-2(S)-phenylthiazolidine-4(S)-carboxylic acid；(2S,4S)-3-acetyl-5,5-dimethyl-2-phenyl-1,3-thiazolidine-4-carboxylic acid
• CAS: 79913-44-3
• 化学式: C₁₄H₁₇NO₃S
• 分子量: 279.36
• InChiKey: KTQBGMMWEAVGEQ-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (-)-(2S,4S)-3-acetyl-5,5-dimethyl-2-phenyl-4-thiazolidinecarboxylic acid 在 乙酸酐 作用下， 反应 0.33h， 以30 mg的产率得到3-acetyl-2(S)-phenyl-5,5-dimethylthiazolidine-4(R)-carboxylic acid
  参考文献：
  名称：

  2-取代的噻唑烷-4-羧酸在C-2的差向异构

  摘要：

  2（R，S）-5,5-Trimethylthiazolidine-4-（S）-羧酸（1a）具有2：3（顺式）异构体的3.3比1的优势，在图2中的C-2位置有差向异构。中性质子溶剂。这通过伴随旋转的nrr谱图中的C-4次甲基质子共振比的变化来证明。化合物1a在稀碳酸钠溶液中稳定，但在1 N盐酸中迅速平衡。

  DOI：

  10.1002/jhet.5570180538
• 作为产物：
  描述：

  D-青霉胺 以 乙醇 、 水 为溶剂， 反应 5.67h， 生成 (-)-(2S,4S)-3-acetyl-5,5-dimethyl-2-phenyl-4-thiazolidinecarboxylic acid
  参考文献：
  名称：

  Synthesis and calcium antagonistic activity of (+)-(R)- and (-)-(S)-3-acetyl-2-(5-methoxy-2-(4-(N-methyl-N-(3,4,5-trimethoxyphenethyl)amino)butoxy)phenyl)benzothiazoline hydrochloride.

  摘要：

  SA2572 ((±)-1)，即3-乙酰基-2-[5-甲氧基-2-[N-甲基-N-(3，4，5-三甲氧基苯乙基)氨基]丁氧基]苯基]-苯并噻唑啉盐酸盐，是一种新合成的Ca2+拮抗剂，具有抑制快速Na+内向通道的作用。为了阐明两种对映体((+)-1和(-)-1)的绝对构型和药理学特性，进行了合成。通过合成前体(5)的X射线晶体学分析，确定了这些化合物的构型。在体外，评估了(+)-1和(-)-1对豚鼠结肠带和兔主动脉去极化诱导收缩的抑制活性，从而评价了它们对Ca2+通道的阻断活性。在体内，通过评估对映体对自发性高血压大鼠的降压效果来评价其疗效。化合物(-)-1在豚鼠结肠带和兔主动脉上表现出比(+)-1更强的Ca2+拮抗活性及降压效果。在Langendorff灌流兔心电生理学研究中，化合物(+)-1对快速Na+内向通道的抑制作用比化合物(-)-1更强，而对慢速Ca2+内向通道的抑制作用与(-)-1相当。发现了药理活性的立体选择性。

  DOI：

  10.1248/cpb.38.936

文献信息

• Thiazolidinecarboxylic acid derivatives and treatment of liver diseases
  申请人：Biogal Gyogyszergyar

  公开号：US04775675A1

  公开（公告）日：1988-10-04

  The invention relates to novel thiazolidine-4(S)-carboxylic acid derivatives of the general formula (I) ##STR1## wherein R.sup.1 stands for an optionally substituted furyl, pyrrolyl, thienyl, benzofuryl, benzopyrrolyl, benzothienyl, phenyl, pyridyl, quinolinyl, isoquinolinyl or indanyl group or a C.sub.1-4 alkyl or C.sub.2-4 alkenyl group optionally substituted by a hydroxyl, carboxyl or halogen fenoxy group, stands for hydrogen, an alkaline metal or an alkaline earth metal atom or an optionally substituted C.sub.1-4 alkyl group or aryl group; R.sup.3 represents hydrogen or an optionally substituted C.sub.1-4 alkyl or acyl group or aryl group as well as their salts. Further on, the invention relates to pharmaceutical preparations containing these compounds and to a process for preparing these compounds and preparations. The compounds of the invention are useful for treating or preventing liver damages of either natural or experimental origin.

  本发明涉及一种新型噻唑烷-4(S)-羧酸衍生物，其一般式为（I）： 其中，R1代表可选取代的呋喃基、吡咯基、噻吩基、苯并呋喃基、苯并吡咯基、苯并噻吩基、苯基、吡啶基、喹啉基、异喹啉基或茚基或C1-4烷基或C2-4烯基，可选取代羟基、羧基或卤代芬氧基；X代表氢、碱金属或碱土金属原子或可选取代的C1-4烷基或芳基；R3代表氢或可选取代的C1-4烷基或酰基或芳基，以及它们的盐。此外，本发明还涉及包含这些化合物的制药制剂以及制备这些化合物和制剂的方法。本发明的化合物可用于治疗或预防自然或实验性起源的肝损伤。
• 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。
• κ opioid receptor agonist comprising 2-phenylbenzothiazoline derivative
  申请人：Santen Pharmaceutical Co., Ltd.

  公开号：US07112598B2

  公开（公告）日：2006-09-26

  A compound or a salt thereof having the following formula wherein R1 is acyl, R2 is hydrogen, halogen, unsubstituted alkyl or alkyl substituted by halogen; R3 is halogen or alkoxy; R4 is cycloalkyl, unsubstituted alkyl or alkyl substituted by cycloalkyl, aryl or hydroxyl or an ester thereof or alkoxy; R5 is hydroxyl or an ester thereof, alkoxy or alkoxyalkyl; or R4 and R5 are bonded with each other to form a pyrrolidine ring substituted by hydroxyl or an ester thereof, alkoxy or alkoxyalkyl; R6 is hydroxyl or an ester thereof, alkoxy, alkoxyalkoxy, alkoxyalkoxyalkoxy, mercapto or alkylthio; and A1 and A2, are the same or different, and are alkylene, provided that (i) when R4 and R5 are bonded to each other to form the pyrrolidine ring substituted by hydroxyl or an ester thereof, R2 is halogen; (ii) when R4 and R5 are bonded to each other to form the pyrrolidine ring substituted by alkoxyalkyl, R2 is hydrogen; (iii) when R6 is hydroxyl or an ester thereof, R4 is isopropyl.

  具有以下式的化合物或其盐，其中R1为酰基，R2为氢，卤素，未取代的烷基或烷基取代的卤素; R3为卤素或烷氧基; R4为环烷基，未取代的烷基或烷基取代的环烷基，芳基或羟基或其酯或烷氧基; R5为羟基或其酯，烷氧基或烷氧基烷基; 或R4和R5彼此连接以形成取代为羟基或其酯，烷氧基或烷氧基烷基的吡咯烷环; R6为羟基或其酯，烷氧基，烷氧基烷氧基，烷氧基烷氧基烷氧基，巯基或烷基硫醚; A1和A2相同或不同，为烷基，前提是（i）当R4和R5连接以形成取代为羟基或其酯的吡咯烷环时，R2为卤素; （ii）当R4和R5连接以形成取代为烷氧基烷基的吡咯烷环时，R2为氢; （iii）当R6为羟基或其酯时，R4为异丙基。
• Method for treating pain or pruritis by administering κ-opioid receptor agonist comprising 2-phenylbenzothiazoline derivative
  申请人：Santen Pharmaceutical Co., Ltd.

  公开号：US07410987B2

  公开（公告）日：2008-08-12

  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 R1 is acyl.

  一种治疗疼痛或瘙痒的方法，包括向需要治疗的患者施用一种药物有效量的κ阿片受体激动剂，其化学式为其中，R是一种烷基，具有氨基官能团作为取代基；R1是酰基。