(2E,4E)-4-(3',4'-dihydro-1'(2'H)-naphthalen-1'-ylidene)-3-methyl-2-butenal | 205252-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (2E,4E)-4-(3',4'-dihydro-1'(2'H)-naphthalen-1'-ylidene)-3-methyl-2-butenal
• 英文别名: (E,4E)-4-(3,4-dihydro-2H-naphthalen-1-ylidene)-3-methylbut-2-enal
• CAS: 205252-44-4
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: NWQILKCGGKIQFX-JZAGDRGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (2E,4E)-4-(3',4'-dihydro-1'(2'H)-naphthalen-1'-ylidene)-3-methyl-2-butenal 在 六甲基磷酰三胺 、 氢氧化钾 、 sodium hydride 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (13Z)-UAB30
  参考文献：
  名称：

  Conformationally Defined Retinoic Acid Analogues. 4. Potential New Agents for Acute Promyelocytic and Juvenile Myelomonocytic Leukemias

  摘要：

  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.

  DOI：

  10.1021/jm970635h
• 作为产物：
  描述：

  (E)-乙基4-溴-3-甲基-2-丁烯酸酯 在 zinc/copper couple 、 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 28.5h， 生成 (2E,4E)-4-(3',4'-dihydro-1'(2'H)-naphthalen-1'-ylidene)-3-methyl-2-butenal
  参考文献：
  名称：

  Conformationally Defined Retinoic Acid Analogues. 5. Large-Scale Synthesis and Mammary Cancer Chemopreventive Activity for (2E,4E,6Z,8E)-8- (3‘,4‘-Dihydro-1‘(2‘H)-naphthalen-1‘-ylidene)-3,7-dimethyl-2,4,6-octatrienoic Acid (9cUAB30)

  摘要：

  Retinoids that activate the nuclear retinoid X receptors (RXRs) display potential for chemo-prevention of breast cancer. We previously reported that 9cUAB30 (1) is an RXR-selective retinoid. To explore its in vivo chemopreventive activity, multigram quantities of 1 were needed. Here, we describe a modified synthesis that yields up to 100 g of 1. We further demonstrate that 1 is very effective in the prevention of N-methyl-N-nitrosourea induced mammary cancers in rats without signs of toxicity.

  DOI：

  10.1021/jm030095q