2-(3,5-diisopropyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one | 180090-36-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3,5-diisopropyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one
• 英文别名: 2-[4-hydroxy-3,5-di(propan-2-yl)phenyl]-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one
• CAS: 180090-36-2
• 化学式: C₁₈H₂₇NO₃S
• 分子量: 337.483
• InChiKey: FJFKFUIBDLZKOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  86.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,5-diisopropyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one 在 氯化亚砜 、 sodium carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 3-(3-{[2-(Benzo[1,3]dioxol-5-yloxy)-ethyl]-methyl-amino}-propyl)-2-(4-hydroxy-3,5-diisopropyl-phenyl)-thiazolidin-4-one
  参考文献：
  名称：

  Novel Calcium Antagonists with Both Calcium Overload Inhibition and Antioxidant Activity. 2. Structure−Activity Relationships of Thiazolidinone Derivatives

  摘要：

  CP-060 (1), 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-[3-[N-methyl-N-[2-[3,4-(methylenedioxy)phenoxy]ethyl]amino]propyl]-1,3-thiazolidin-4-one, is a novel type of Ca2+ antagonist possessing both Ca2+ overload inhibition and antioxidant activity. The structure-activity relationships for this series of compounds were studied by synthesizing the analogues and evaluating these three kinds of activity. Ca2+ antagonistic activity was largely determined by the lipophilicity of the phenyl group at the 2-position and the length of the alkyl chains. As for-the antioxidant activity, it was demonstrated that the phenolic hydroxyl group is an essential structural element. Compounds with potent activity were! evaluated for their effect on the coronary blood flow in vivo. Among these compounds, compound 1 was shown to be the most potent. Furthermore, the enantiomers of 1 were resolved by high-performance liquid chromatography with a chiral column. Compound (-)-1 showed about 10 times higher Ca2+ antagonistic activity than (+)-1, though both enarrtiomers had similar potency in Ca2+ overload inhibition and antioxidant activity. An X-ray crystal structure determination of (-)-1 hydrogen fumarate identified (-)-1 as having S configuration at the 2-position.

  DOI：

  10.1021/jm9900927
• 作为产物：
  描述：

  4-羟基-3,5-二异丙基苯甲醛 以 苯 为溶剂， 反应 3.5h， 生成 2-(3,5-diisopropyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Novel Calcium Antagonists with Both Calcium Overload Inhibition and Antioxidant Activity. 2. Structure−Activity Relationships of Thiazolidinone Derivatives

  摘要：

  CP-060 (1), 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-[3-[N-methyl-N-[2-[3,4-(methylenedioxy)phenoxy]ethyl]amino]propyl]-1,3-thiazolidin-4-one, is a novel type of Ca2+ antagonist possessing both Ca2+ overload inhibition and antioxidant activity. The structure-activity relationships for this series of compounds were studied by synthesizing the analogues and evaluating these three kinds of activity. Ca2+ antagonistic activity was largely determined by the lipophilicity of the phenyl group at the 2-position and the length of the alkyl chains. As for-the antioxidant activity, it was demonstrated that the phenolic hydroxyl group is an essential structural element. Compounds with potent activity were! evaluated for their effect on the coronary blood flow in vivo. Among these compounds, compound 1 was shown to be the most potent. Furthermore, the enantiomers of 1 were resolved by high-performance liquid chromatography with a chiral column. Compound (-)-1 showed about 10 times higher Ca2+ antagonistic activity than (+)-1, though both enarrtiomers had similar potency in Ca2+ overload inhibition and antioxidant activity. An X-ray crystal structure determination of (-)-1 hydrogen fumarate identified (-)-1 as having S configuration at the 2-position.

  DOI：

  10.1021/jm9900927

文献信息

• BENZENE DERIVATIVE USEFUL FOR ISCHEMIC DISEASES
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0705816A1

  公开（公告）日：1996-04-10

  Compounds represented by formula (I): wherein, for example, R₁, R₂, R₃, and R₄ each represents a hydrogen atom; R₆ and R₇ each represent a substituted or unsubstituted lower alkyl group; A represents a group represented by formula (II): wherein R₅ represents, for example, a hydrogen atom; and n represents an integer of 2 to 6, or a possible stereoisomer or optical isomer thereof and a pharmaceutically acceptable salt thereof. The compounds represented by formula (I) have an inhibitory action on calcium overload in addition to a vasorelaxing activity (calcium antagonism) and an inhibitory action on lipid peroxidation and are useful as a preventive or treating agent for ischemic diseases and a hypertension.

  式 (I) 所代表的化合物： 其中，R₁、R₂、R₃ 和 R₄ 各自代表氢原子；R₆ 和 R₇ 各自代表取代或未取代的低级烷基；A 代表式 (II) 所代表的基团： 其中 R₅ 代表例如氢原子；n 代表 2 至 6 的整数，或其可能的立体异构体或光学异构体及其药学上可接受的盐。式 (I) 所代表的化合物除了具有血管舒张活性（钙离子拮抗作用）和脂质过氧化抑制作用外，还具有抑制钙超载的作用，可用作缺血性疾病和高血压的预防或治疗药物。
• REMEDY FOR ISCHEMIC DISEASES
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：EP0799614A1

  公开（公告）日：1997-10-08

  A compound represented by general formula (I), possible stereoisomer and optical isomer thereof, and pharmaceutically acceptable salts thereof, wherein R1, R2, R3 and R4 represent each hydrogen, etc.; R6 and R7 represent each optionally substituted lower alkyl; A represents a group of general formula (II) (wherein R5 represents hydrogen, etc.); and n is an integer of from 2 to 6. These compounds can suppress the formation of active oxygen and an increase in intracellular calcium and thus are useful as a remedy for ischemic diseases.

  通式（I）代表的化合物、其可能的立体异构体和光学异构体及其药学上可接受的盐，其中 R1、R2、R3 和 R4 分别代表氢等；R6 和 R7 分别代表任选取代的低级烷基；A 代表通式（II）的基团（其中 R5 代表氢等）；n 为 2 至 6 的整数。这些化合物可抑制活性氧的形成和细胞内钙的增加，因此可用于治疗缺血性疾病。
• US5998452
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• EP799614
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• US05998452
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