trans-3-(1',2',3',4'-tetrahydro-6'-naphthyl)propenal | 150012-40-1

• 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-6'-naphthyl)propenal
• 英文别名: (E)-3-(5,6,7,8-tetrahydronaphthalen-2-yl)but-2-enal
• CAS: 150012-40-1
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: KEXAVFSALGIVLM-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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-6'-naphthyl)propenal 在 吡啶 、 氢氧化钾 、 三乙基硼氢化钠 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 172.75h， 生成
  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：

  6-乙酰基-1,2,3,4-四氢萘 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 64.5h， 生成 trans-3-(1',2',3',4'-tetrahydro-6'-naphthyl)propenal
  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

文献信息

• NOVEL COMPOUNDS
  申请人：Smithkline Beecham S.p.A.

  公开号：EP0802897A1

  公开（公告）日：1997-10-29
• [EN] NOVEL COMPOUNDS<br/>[FR] COMPOSES NOUVEAUX
  申请人：SMITHKLINE BEECHAM S.P.A.

  公开号：WO1996021638A1

  公开（公告）日：1996-07-18

  (EN) A compound of formula (I), or a salt thereof, or a solvate thereof, wherein: R1 is an alkyl group or a substituted or unsubstituted phenyl group; R2 and R3 each independently represent hydrogen or alkyl; and either: RA represents T1 wherein T1 is hydrogen or alkyl; and RB represents a moiety of formula (a) wherein T2 and T3 each independently represents hydrogen, hydroxy, amino, alkoxy, alkylcarbonyloxy, optionally substituted phenoxy, optionally substituted benzyloxy, alkylamino, dialkylamino, chloro, alkyl, carboxy, carbalkoxy, carbamoyl, alkylcarbamoyl or T2 and T3 together represent a C3-5-alkylene chain each carbon atom of which is optionally substituted with up to three alkyl groups; or RA together with RB represents a moiety of formula (b), wherein R4, R5, R8 and R9 each independently represents hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl or R4 and R5 together with the carbon atoms to which they are attached or R8 and R9 together with the carbon atomsto which they are attached form an optionally substituted phenylene ring; and R6 and R7 each independently represent hydrogen, alkyl, aryl, alkoxy; or R6 and R7 together with the carbon atom to which they are attached form a saturated heterocyclic ring; or RA represents a moiety of formula (c) and RB represents a moiety of formula (d), wherein T4, T5, T6 and T7 each independently represents hydrogen, alkoxy, alkylcabonyloxy, optionally substituted phenoxy, optionally substituted benzyloxy, alkylamino, dialkylamino, chloro, alkyl, carboxy, carbalkoxy, carbamoyl or alkylcarbamoyl; and X1 and Y each independently represents hydrogen or X1 together with Y represents a C3-5-alkylene chain, a moiety of formula -CO-NH-, -CH2-NH- or -CH2-O-; and X represents hydroxy, alkoxy or a group of formula NRsRt wherein Rs and Rt each independently represents hydrogen, alkyl, substituted alkyl, phenyl, substituted phenyl, phenylalkyl or heteroarylalkyl; or Rs and Rt together with the nitrogen atom to which they are attached represent a saturated heterocyclic group; a process for the preparation of such a compound, a pharmaceutical composition comprising such a compound and the use of such a compound in medicine.(FR) Composé de la formule (I), ou un sel ou solvate de celui-ci, dans laquelle: R1 représente un groupe alkyle ou un groupe phényle substitué ou non; R2 et R3 représentent chacun indépendamment hydrogène ou alkyle; et soit: RA représente T1, T1 représentant hydrogène ou alkyle; et RB représente une fraction de la formule (a) dans laquelle T2 et T3 représentent chacun indépendamment hydrogène, hydroxy, amino, alcoxy, alkylcarbonyloxy, phénoxy éventuellement substitué, benzyloxy éventuellement substitué, alkylamino, dialkylamino, chloro, alkyle, carboxy, carbalcoxy, carbamoyle, alkylcarbamoyle, ou bien T2 et T3 représentent ensemble une chaîne alkylène C3-5 dont chaque atome de carbone est éventuellement substitué par trois groupes alkyle au maximum; soit: RA, ensemble avec RB, représente une fraction de la formule (b) dans laquelle R4, R5, R8 et R9 représentent chacun indépendamment hydrogène, alkyle, alkyle substitué, aryle, aryle substitué, aralkyle, ou R4 et R5, avec les atomes de carbone auxquels ils sont attachés, ou R8 et R9 avec les atomes de carbone auxquels ils sont attachés, forment un noyau phénylène éventuellement substitué; et R6 et R7 représentent chacun indépendamment hydrogène, alkyle, aryle, alcoxy; ou bien R6 et R7, ensemble avec l'atome de carbone auquel ils sont attachés, forment un noyau hétérocyclique saturé; soit encore: RA représente une fraction de la formule (c) et RB représente une fraction de la formule (d), formules dans lesquelles T4, T5, T6 et T7 représentent chacun indépendamment hydrogène, alcoxy, alkylcarbonyloxy, phénoxy éventuellement substitué, benzyloxy éventuellement substitué, alkylamino, dialkylamino, chloro, alkyle, carboxy, carbalcoxy, carbamoyle ou alkylcarbamoyle; et X1 et Y représentent chacun indépendamment hydrogène, ou bien X1 ensemble avec Y représente une chaîne alkylène C3-5, une fraction de formule -CO-NH-, -CH2-NH-, ou -CH2O-; et X représente hydroxy, alcoxy ou un groupe de formule NRsRt dans lequel Rs et Rt représentent chacun indépendamment hydrogène, alkyle, alkyle substitué, phényle, phényle substitué, phénylalkyle ou hétéroarylalkyle; ou bien Rs et Rt, ensemble avec l'atome d'azote auquel ils sont attachés, représentent un groupe hétérocyclique saturé. On décrit également un procédé de préparation d'un tel composé, une composition pharmaceutique comprenant celui-ci ainsi que l'utilisation de ce composé en médecine.
• ——
  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.