trans-3-(1',2',3',4'-tetrahydro-1',1',4',4'-tetramethyl-6'-naphthyl)propenal | 177741-09-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: trans-3-(1',2',3',4'-tetrahydro-1',1',4',4'-tetramethyl-6'-naphthyl)propenal
• 英文别名: (E)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-enal；(E)-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)but-2-enal
• CAS: 177741-09-2
• 化学式: C₁₈H₂₄O
• 分子量: 256.388
• InChiKey: KQOVUBWRIZBWJE-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  trans-3-(1',2',3',4'-tetrahydro-1',1',4',4'-tetramethyl-6'-naphthyl)propenal 在 吡啶 、 氢氧化钾 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 216.0h， 生成 (2Z,4E,6E)-4-Hydroxymethyl-3-methyl-7-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-octa-2,4,6-trienoic acid
  参考文献：
  名称：

  摘要：

  Purpose. Optimization of the therapeutic ratio of analogs of the topically active 11-cis, 13-cis-12-hydroxymethylretinoic acid, delta-lactone (1) relative to antihyperproliferation and antihyperkeratinization vs. toxicity. Methods. Nine analogs of 1, in which variations were made in the lipophilic cyclohexenyl moiety or in the lactone ring, were evaluated for topical activity against hyperkeratinization, inhibition of TPA-induced DNA synthesis and for skin irritation. Results. Although more potent lactones than the parent lactone 1 were identified, none possessed the favorable therapeutic ratio associated with 1. Conclusions. The delta-lactone 1 possesses unique molecular features responsible for its desirable therapeutic ratio as an antihyperproliferative and antihyperkeratotic agent. In view of its very low systemic retinoid toxicity and the absence of any systemic toxicity, this lactone may be a good candidate for use in the topical treatment of acne.

  DOI：

  10.1023/a:1016250129246
• 作为产物：
  描述：

  (E)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-en-1-ol 在 二氧化锰 作用下， 以 二氯甲烷 为溶剂， 以afforded 2.86 g of (E)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-enal as pale yellow oil的产率得到trans-3-(1',2',3',4'-tetrahydro-1',1',4',4'-tetramethyl-6'-naphthyl)propenal
  参考文献：
  名称：

  Retinoic acid X-receptor ligands

  摘要：

  公式(I)的化合物中，R.sup.1-R.sup.7、R.sup.10、X和点状键具有规范中给出的含义，它们选择性地结合到视黄酸RXR受体上，并且作为皮肤和肿瘤学适应症的抗增殖剂有用。

  公开号：

  US05801253A1

文献信息

• RETINOIC ACID X-RECEPTOR LIGANDS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0775103A1

  公开（公告）日：1997-05-28
• US5801253A
  申请人：——

  公开号：US5801253A

  公开（公告）日：1998-09-01
• [EN] RETINOIC ACID X-RECEPTOR LIGANDS<br/>[FR] LIGANDS DES RECEPTEURS X DE L'ACIDE RETINOIQUE
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：WO1996005165A1

  公开（公告）日：1996-02-22

  (EN) Compounds of formula (I) wherein R1-R7, R10, X and the dotted bond have the meaning given in the specification, bind selectively to retinoid RXR receptors and are useful as antiproliferative agents for dermatological and oncological indications.(FR) Des composés de la formule (I), dans laquelle R1-R7, R10, X et la liaison en pointillé ont la notation donnée dans la description, se fixent sélectivement aux récepteurs RXR rétinoïdes et sont utiles comme agents antiprolifératifs pour des indications dermatologiques et oncologiques.
• Retinoic acid X-receptor ligands
  申请人：Hoffmann-La Roche Inc.

  公开号：US05801253A1

  公开（公告）日：1998-09-01

  Compounds of formula (I) wherein R.sup.1 -R.sup.7, R.sup.10, X and the dotted bond have the meaning given in the specification, bind selectively to retinoid RXR receptors and are useful as antiproliferative agents for dermatological and oncological indications.

  式（I）中的化合物，其中R.sup.1 -R.sup.7，R.sup.10，X和点线键具有规范中给定的含义，可选择性地结合到视黄醇RXR受体，并可用作皮肤病和肿瘤学适应症的抗增殖剂。
• ——
  作者：Anita H. Lewin、Sherry L. Black、Mary E. Bos、R. Richard Goehring、Xina Nair、Gary Whiting、Pamela Bouquin、Geraldine Tetrault、F. Ivy Carroll

  DOI：10.1023/a:1016250129246

  日期：——

  Purpose. Optimization of the therapeutic ratio of analogs of the topically active 11-cis, 13-cis-12-hydroxymethylretinoic acid, delta-lactone (1) relative to antihyperproliferation and antihyperkeratinization vs. toxicity. Methods. Nine analogs of 1, in which variations were made in the lipophilic cyclohexenyl moiety or in the lactone ring, were evaluated for topical activity against hyperkeratinization, inhibition of TPA-induced DNA synthesis and for skin irritation. Results. Although more potent lactones than the parent lactone 1 were identified, none possessed the favorable therapeutic ratio associated with 1. Conclusions. The delta-lactone 1 possesses unique molecular features responsible for its desirable therapeutic ratio as an antihyperproliferative and antihyperkeratotic agent. In view of its very low systemic retinoid toxicity and the absence of any systemic toxicity, this lactone may be a good candidate for use in the topical treatment of acne.