(2Z,4E)-4-(3',4'-dihydro-1'(2'H)-naphthalen-1'-ylidene)-3-methyl-2-buten-1-ol | 205252-38-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (2Z,4E)-4-(3',4'-dihydro-1'(2'H)-naphthalen-1'-ylidene)-3-methyl-2-buten-1-ol
• 英文别名: (Z,4E)-4-(3,4-dihydro-2H-naphthalen-1-ylidene)-3-methylbut-2-en-1-ol
• CAS: 205252-38-6
• 化学式: C₁₅H₁₈O
• 分子量: 214.307
• InChiKey: LPIIDASSLAVPJZ-MMFCQQQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2Z,4E)-4-(3',4'-dihydro-1'(2'H)-naphthalen-1'-ylidene)-3-methyl-2-buten-1-ol 在 lithium aluminium tetrahydride 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 、 丙酮 为溶剂， 反应 2.0h， 生成 (2E,4E,6Z,8E)-ethyl 8-(3',4'-dihydro-1'(2'H)-naphthalen-1'-ylidene)-3,7-dimethyl-2,4,6-octatrienoate
  参考文献：
  名称：

  [EN] PROCESS FOR THE SYNTHESIS OF (2E, 4E, 6Z, 8E)-8-(3,4-DIHYDRONAPHTHALEN-1(2H)-YLIDENE)-3,7-DIMETHYLOCTA-2, 4, 6-TRIENOIC ACID
  [FR] PROCÉDÉ DE SYNTHÈSE DE L'ACIDE (2E, 4E, 6Z, 8E)-8-(3,4-DIHYDRONAPHTHALEN-1(2H)-YLIDÈNE)-3,7-DIMÉTHYLOCTA-2,4,6-TRIÉNOÏQUE

  摘要：

  本发明涉及一种合成(2E,4E,6Z,8E)-8-(3,4-二氢萘-1(2H)-亚基)-3,7-二甲基-2,4,6-辛三烯酸的新方法。特别是，本发明涉及在多步合成方案中的几个单独步骤的几项改进。

  公开号：

  WO2017158023A1
• 作为产物：
  描述：

  3-甲基-2-丁烯酸乙酯 在 lithium aluminium tetrahydride 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 甲基叔丁基醚 、 乙基苯 、 丙酮 、 甲苯 为溶剂， 反应 7.0h， 生成 (2Z,4E)-4-(3',4'-dihydro-1'(2'H)-naphthalen-1'-ylidene)-3-methyl-2-buten-1-ol
  参考文献：
  名称：

  [EN] PROCESS FOR THE SYNTHESIS OF (2E, 4E, 6Z, 8E)-8-(3,4-DIHYDRONAPHTHALEN-1(2H)-YLIDENE)-3,7-DIMETHYLOCTA-2, 4, 6-TRIENOIC ACID
  [FR] PROCÉDÉ DE SYNTHÈSE DE L'ACIDE (2E, 4E, 6Z, 8E)-8-(3,4-DIHYDRONAPHTHALEN-1(2H)-YLIDÈNE)-3,7-DIMÉTHYLOCTA-2,4,6-TRIÉNOÏQUE

  摘要：

  本发明涉及一种合成(2E,4E,6Z,8E)-8-(3,4-二氢萘-1(2H)-亚基)-3,7-二甲基-2,4,6-辛三烯酸的新方法。特别是，本发明涉及在多步合成方案中的几个单独步骤的几项改进。

  公开号：

  WO2017158023A1

文献信息

• Methods for making retinoids and uses thereof
  申请人：Brouillette Wayne J.

  公开号：US20100204327A1

  公开（公告）日：2010-08-12

  Described herein are methods for making retinoids. Also described herein are retinoids and methods of use thereof.

  本文描述了制备视黄醇类化合物的方法。同时也描述了视黄醇类化合物及其使用方法。
• METHODS FOR MAKING RETINOIDS AND USES THEREOF
  申请人：The UAB Research Foundation

  公开号：US20160106697A1

  公开（公告）日：2016-04-21

  Described herein are methods for making retinoids. Also described herein are retinoids and methods of use thereof.

  本文描述了制备视黄醇的方法。同时还描述了视黄醇及其使用方法。
• Retinoids useful in the treatment of cancer and for reducing serum triglycerides
  申请人：The UAB Research Foundation

  公开号：EP2292576A2

  公开（公告）日：2011-03-09

  The present invention relates to a compound having the formula XXX or wherein R1 is a C5 or greater branched or straight chain alkyl group; R2 is hydrogen, a C1-C15 branched or straight chain alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted cycloalkyl group, or R1 and R2 collectively form a substituted or unsubstituted fused aryl group; and R3 is one or more groups comprising, independently, hydrogen, a C1-C15 branched or straight chain alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted cycloalkyl group; R6 and R7 are, independently, hydrogen, a C1-C15 branched or straight chain alkyl group, or a substituted or unsubstituted cycloalkyl group; R11 is hydrogen or a C1-C15 branched or straight chain alkyl group; and n is from 0 to 3, wherein one or more carbon atoms in the ring in formula XXX can optionally be replaced with a heteroatom, or the pharmaceutically-acceptable salt or ester thereof, wherein the compound is not (2E,4E,6Z,8E)-8-(3',4'-dihydro-1'(2'H-naphthalen-1'-ylidene))-3,7-dimethyl-2,4,6-octatrienoic acid or an ester thereof; (2E,4E,6E,8E)-8-(3',4'-dihydro-1'(2'H-naphthalen-1'-ylidene))-3,7-dimethyl-2,4,6-octatrienoic acid or an ester thereof; (2E,4E,6Z,8E)-8-(3',4'-dihydro-4'methyl-1'(2'H-naphthalen-1'-ylidene))-3,7-dimethyl-2,4,6-octatrienoic acid or an ester thereof; and (2E,4E,6Z,8E)-8-(3',4'-dihydro-5',7'-dimethyl-1'(2'H-naphthalen-1'-ylidene))-3,7-dimethyl-2,4,6-octatrienoic acid or an ester thereof.

  本发明涉及一种具有式 XXX 的化合物 或 其中 R1 是 C5 或更大的支链或直链烷基； R2 是氢、C1-C15 支链或直链烷基、取代或未取代的芳基、取代或未取代的芳烷基或取代或未取代的环烷基，或 R1 和 R2 共同形成取代或未取代的融合芳基；和 R3 是一个或多个基团，独立地包括氢、C1-C15 支链或直链烷基、取代或未取代的芳基、取代或未取代的芳烷基或取代或未取代的环烷基； R6 和 R7 独立地为氢、C1-C15 支链或直链烷基或取代或未取代的环烷基； R11 是氢或 C1-C15 支链或直链烷基；以及 n 是 0 至 3、 其中式 XXX 中环的一个或多个碳原子可任选被杂原子取代，或其药学上可接受的盐或酯、 其中化合物不是(2E,4E,6Z,8E)-8-(3',4'-二氢-1'(2'H-萘-1'-亚基))-3,7-二甲基-2,4,6-辛三烯酸或其酯；(2E,4E,6E,8E)-8-(3',4'-二氢-1'(2'H-萘-1'-亚基))-3,7-二甲基-2,4,6-辛三烯酸或其酯；(2E,4E,6Z,8E)-8-(3',4'-二氢-4'甲基-1'(2'H-萘-1'-亚基))-3,7-二甲基-2,4,6-辛三烯酸或其酯；和 (2E,4E,6Z,8E)-8-(3',4'-二氢-5',7'-二甲基-1'(2'H-萘-1'-亚基))-3,7-二甲基-2,4,6-辛三烯酸或其酯。
• [EN] METHODS FOR MAKING RETINOIDS AND USES THEREOF<br/>[FR] PROCEDES DE FABRICATION DE RETINOIDES ET LEURS UTILISATIONS
  申请人：UAB RESEARCH FOUNDATION

  公开号：WO2006036394A3

  公开（公告）日：2006-08-17
• Conformationally Defined Retinoic Acid Analogues. 4. Potential New Agents for Acute Promyelocytic and Juvenile Myelomonocytic Leukemias
  作者：Donald D. Muccio、Wayne J. Brouillette、Theodore R. Breitman、Mohammed Taimi、Peter D. Emanuel、Xiao-kun Zhang、Guo-quan Chen、Brahma P. Sani、Pratap Venepally、Lakshmi Reddy、Muzaffar Alam、Linda Simpson-Herren、Donald L. Hill

  DOI：10.1021/jm970635h

  日期：1998.5.1

  We recently synthesized several conformationally constrained retinoic acid (RA) analogues [8-(2'-cyclohexen-1'-ylidene)-3,7-dimethyl-2,4,6-octatrienoic acids with different alkyl substituents at 2' (R-1) and 3' (R-2) positions on the cyclohexene ring] (Muccio et al. J. Med. Chem. 1996, 39, 3625) as cancer chemopreventive agents. UAB8 (R-1 = Et; R-2 = Pr-i), which contains sufficient steric bulk at the terminal end of the polyene chain to mimic the trimethylcyclohexenyl ring of RA, displayed biological properties similar to those of RA. To explore the efficacy of this retinoid in acute promyelocytic leukemia (APL) and juvenile myelomonocytic leukemia (JMML), we evaluated UAB8 isomers in in vitro assays which measure the capacity of retinoids to inhibit aberrant myeloid colony growth from blood or bone marrow cells obtained from human JMML patients and in assays measuring the potential of retinoids to differentiate NB4 cells tan APL cell line). Both (all-E)- and (13Z)-UAB8 were 2-fold more active than RA in the NB4 cell differentiation assay; however, only (all-E)-UAB8 had comparable activity to the natural retinoids in the JMML cell assays. These results were compared to the biological effectiveness of a new retinoid, UAB30 [8-(3',4'-dihydro-1'(2'H)-naphthalen-1'-ylidene)-3,7-dimethyl-2,4,6-octatrienoic acid], which had different nuclear receptor binding and transactivational properties than UAB8. Relative to (all-E)-RA and (all-E)-UAB8, (all-E)-UAB30 bound well to RAR alpha but did not activate transcription-mediated RAR alpha homodimers, even though it was effective in RAR beta- and RAR gamma-mediated transactivational assays. In APL assays, this retinoid had much reduced activity and was only moderately effective in JMML assays and in cancer chemoprevention assays.