4-((S)-8-Hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-benzoic acid ethyl ester | 226250-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 4-((S)-8-Hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-benzoic acid ethyl ester
• 英文别名: Benzoic acid, 4-(((8S)-5,6,7,8-tetrahydro-8-hydroxy-5,5-dimethyl-2-naphthalenyl)ethynyl)-, ethyl ester；ethyl 4-[2-[(8S)-8-hydroxy-5,5-dimethyl-7,8-dihydro-6H-naphthalen-2-yl]ethynyl]benzoate
• CAS: 226250-06-2
• 化学式: C₂₃H₂₄O₃
• 分子量: 348.442
• InChiKey: RKAVXDSAMZQAFH-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-((S)-8-Hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-benzoic acid ethyl ester 在 lithium hydroxide 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 4-[(S)-5,5-Dimethyl-8-(tetrahydro-pyran-2-yloxy)-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-benzoic acid
  参考文献：
  名称：

  A New Class of RAR Subtype Selective Retinoids: Correlation of Pharmacological Effects with Receptor Activity

  摘要：

  The synthesis and biological activity of a series of structurally related retinoids with different RAR subtype selectivities are described. These retinoids bind to all three RAR subtypes but in functional transactivation assays, they show RAR beta or RAR beta,gamma selectivity with weak RAR alpha activity. The subtype selectivity of these retinoids was found to correlate with their efficacy (ODC inhibition) and toxicity (topical irritation and teratogenicity) profiles. The degree of RAR gamma transactivation activity correlates with their topical toxicity and teratogenicity as measured by the inhibition of chondrogenesis. Of the RAR beta selective retinoids reported here, retinoid 12 is the most promising, as it is completely devoid of two common retinoid related toxicities, namely topical irritation and teratogenesis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00212-0
• 作为产物：
  描述：

  4-[(5,6,7,8-四氢-5,5-二甲基-8-氧代-2-萘)乙炔]苯甲酸乙酯 在 二乙醇胺 、 (-)-diisopinocamphenylborane chloride 作用下， 生成 4-((R)-8-Hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-benzoic acid ethyl ester 、 4-((S)-8-Hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl)-benzoic acid ethyl ester
  参考文献：
  名称：

  A New Class of RAR Subtype Selective Retinoids: Correlation of Pharmacological Effects with Receptor Activity

  摘要：

  The synthesis and biological activity of a series of structurally related retinoids with different RAR subtype selectivities are described. These retinoids bind to all three RAR subtypes but in functional transactivation assays, they show RAR beta or RAR beta,gamma selectivity with weak RAR alpha activity. The subtype selectivity of these retinoids was found to correlate with their efficacy (ODC inhibition) and toxicity (topical irritation and teratogenicity) profiles. The degree of RAR gamma transactivation activity correlates with their topical toxicity and teratogenicity as measured by the inhibition of chondrogenesis. Of the RAR beta selective retinoids reported here, retinoid 12 is the most promising, as it is completely devoid of two common retinoid related toxicities, namely topical irritation and teratogenesis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00212-0

文献信息

• A New Class of RAR Subtype Selective Retinoids: Correlation of Pharmacological Effects with Receptor Activity
  作者：Vidyasagar Vuligonda、Yuan Lin、Scott M. Thacher、Andrew M. Standeven、Devendra M. Kochar、Roshantha A.S. Chandraratna

  DOI：10.1016/s0968-0896(98)00212-0

  日期：1999.2

  The synthesis and biological activity of a series of structurally related retinoids with different RAR subtype selectivities are described. These retinoids bind to all three RAR subtypes but in functional transactivation assays, they show RAR beta or RAR beta,gamma selectivity with weak RAR alpha activity. The subtype selectivity of these retinoids was found to correlate with their efficacy (ODC inhibition) and toxicity (topical irritation and teratogenicity) profiles. The degree of RAR gamma transactivation activity correlates with their topical toxicity and teratogenicity as measured by the inhibition of chondrogenesis. Of the RAR beta selective retinoids reported here, retinoid 12 is the most promising, as it is completely devoid of two common retinoid related toxicities, namely topical irritation and teratogenesis. (C) 1999 Elsevier Science Ltd. All rights reserved.