5-{1-[3,8-dimethyl-5-(1-methylethyl)azulenyl]}-3-methyl-2,4-pentadienal | 137811-17-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 5-{1-[3,8-dimethyl-5-(1-methylethyl)azulenyl]}-3-methyl-2,4-pentadienal
• 英文别名: (2E,4E)-5-(3,8-dimethyl-5-propan-2-ylazulen-1-yl)-3-methylpenta-2,4-dienal
• CAS: 137811-17-7
• 化学式: C₂₁H₂₄O
• 分子量: 292.421
• InChiKey: AETKBNBENHOMFZ-UYLQCNQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  5-{1-[3,8-dimethyl-5-(1-methylethyl)azulenyl]}-3-methyl-2,4-pentadienal 在 氢氧化钾 、 lithium diisopropyl amide 作用下， 以 甲醇 、 水 为溶剂， 反应 2.75h， 生成 3,7-dimethyl-9-<1-<3,8-dimethyl-5-(1-methylethyl)azulenyl>>-2,4,6,8-nonatetraenoic acid
  参考文献：
  名称：

  Azulenic retinoids: novel nonbenzenoid aromatic retinoids with anticancer activity

  摘要：

  Several novel azulene-containing retinoids were prepared and evaluated for their ability to suppress carcinogen-induced neoplastic transformation and to concomitantly up-regulate gap junctional communication in the in vitro mouse fibroblast C3H/10T1/2 cell bioassay. The azulenic retinoids were divided into two groups: compounds 1-6 were modeled after retinoic acid with flexible polyenic side chain whereas retinoids 7-13 featured a benzoic acid moiety analogous to the prototypic retinobenzoate (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl]benzoic acid (TTNPB). Within this latter group the side chains for compounds 7, 10, and 11 were attached at the 1-, 2-, and 8-positions of the azulenic terminus, respectively. Biological activities were determined for all the new compounds. Two of these novel retinoids, azulenic retinobenzoic acid derivatives 7 and 11, were completely effective inhibitors of transformation at 10(-6) M. The most active azulenic retinoids also enhanced gap junctional communication in untransformed cells; this was associated with up-regulated expression of connexin 43, a structural protein of the gap junction. Two fluorinated analogs were also tested. The azulenic fluoro acid 5 was found to be more potent than the trifluoromethyl analog 6. Azulenic analogs with hydroxyl or carboxaldehyde side chain functional groups were ineffective transformation inhibitors. In general, azulenic retinobenzoic acid analogs structurally akin to TTNPB were more effective than flexible side chain analogs related to retinoic acid.

  DOI：

  10.1021/jm00073a013
• 作为产物：
  描述：

  3-甲酰基愈创葵 在 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.92h， 生成 5-{1-[3,8-dimethyl-5-(1-methylethyl)azulenyl]}-3-methyl-2,4-pentadienal
  参考文献：
  名称：

  Azulenic retinoids: novel nonbenzenoid aromatic retinoids with anticancer activity

  摘要：

  Several novel azulene-containing retinoids were prepared and evaluated for their ability to suppress carcinogen-induced neoplastic transformation and to concomitantly up-regulate gap junctional communication in the in vitro mouse fibroblast C3H/10T1/2 cell bioassay. The azulenic retinoids were divided into two groups: compounds 1-6 were modeled after retinoic acid with flexible polyenic side chain whereas retinoids 7-13 featured a benzoic acid moiety analogous to the prototypic retinobenzoate (E)-4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1-propenyl]benzoic acid (TTNPB). Within this latter group the side chains for compounds 7, 10, and 11 were attached at the 1-, 2-, and 8-positions of the azulenic terminus, respectively. Biological activities were determined for all the new compounds. Two of these novel retinoids, azulenic retinobenzoic acid derivatives 7 and 11, were completely effective inhibitors of transformation at 10(-6) M. The most active azulenic retinoids also enhanced gap junctional communication in untransformed cells; this was associated with up-regulated expression of connexin 43, a structural protein of the gap junction. Two fluorinated analogs were also tested. The azulenic fluoro acid 5 was found to be more potent than the trifluoromethyl analog 6. Azulenic analogs with hydroxyl or carboxaldehyde side chain functional groups were ineffective transformation inhibitors. In general, azulenic retinobenzoic acid analogs structurally akin to TTNPB were more effective than flexible side chain analogs related to retinoic acid.

  DOI：

  10.1021/jm00073a013

文献信息

• COMPOSITIONS COMPRISING VARIOUS PROTEORHODOPSINS AND/OR BACTERIORHODOPSINS AND USE THEREOF
  申请人：Danisco US Inc.

  公开号：EP1753448B1

  公开（公告）日：2012-04-25
• Photochromic Material Comprising a Proteorhodopsin Apoprotein and a Retinal Analog
  申请人：Jensen Rasmus B.

  公开号：US20080290328A1

  公开（公告）日：2008-11-27

  The present invention relates to a photochromic material comprising a proteorhodopsin apoprotein and a retinal analog. In one embodiment, the retinal analog is an azulenic retinoid compound. In another embodiment, the retinal analog is a compound that is structurally similarly to all-trans-retinal. The proteorhodopsin apoprotein and the retinal analog form a photochromic material having different spectral properties from those of a corresponding photochromic material formed by the same proteorhodopsin apoprotein and all-trans-retinal. In one embodiment of the application, the retinal analog-containing proteorhodopsin has an absorbance spectrum that does not overlap significantly with that of all-trans-retinal-containing proteorhodopsin. In another embodiment of the application, the retinal analog-containing proteorhodopsin yields a red-shifted visual chromophore compared with the all-trans-retinal-containing proteorhodopsin chromophore. The photochromic material of the present invention is useful as an optical data storage carrier, a fraud-proof optical data carrier, security ink, and in other optical applications.
• Composition Comprising Various Proteorhodopsins and/or Bacteriorhodopsins and Use Thereof
  申请人：Bott Richard R.

  公开号：US20080292828A1

  公开（公告）日：2008-11-27

  The present invention provides a solid material comprising an immobilized mixture of two or more proteorhodopsins, two or more bacteriorhodopsins, or one or more bacteriorhodopsin and one or more proteorhodopsins. The proteorhodopsins are selected from the group consisting of all-trans-retinal-containing proteorhodopsins and retinal analog-containing proteorhodopsins; all of which have absorption spectra that do not overlap. The bacteriorhodopsins are selected from the group consisting of all-trans-retinal-containing bacteriorhodopsins and retinal analog-containing bacteriorhodopsins; all of which have absorption spectra that do not overlap. The present invention also provides an optical information carrier, such as an optical data storage material and a fraud-proof optical data carrier, comprising the above-described solid material and a substrate selected from the group consisting of glass, paper, metal, fabric material, and plastic material, wherein said solid material is deposited on said substrate. The present invention further provides security ink comprising one or more hydrophilic polymers and a mixture of various photochromic materials.
• COMPOSITION COMPRISING VARIOUS PROTEORHODOPSINS AND/OR BACTERIORHODOPSINS AND USE THEREOF
  申请人：Bott Richard R.

  公开号：US20120010333A1

  公开（公告）日：2012-01-12

  The present invention provides a solid material comprising an immobilized mixture of two or more proteorhodopsins, two or more bacteriorhodopsins, or one or more bacteriorhodopsin and one or more proteorhodopsins. The proteorhodopsins are selected from the group consisting of all-trans-retinal-containing proteorhodopsins and retinal analog-containing proteorhodopsins; all of which have absorption spectra that do not overlap. The bacteriorhodopsins are selected from the group consisting of all-trans-retinal-containing bacteriorhodopsins and retinal analog-containing bacteriorhodopsins; all of which have absorption spectra that do not overlap. The present invention also provides an optical information carrier, such as an optical data storage material and a fraud-proof optical data carrier, comprising the above-described solid material and a substrate selected from the group consisting of glass, paper, metal, fabric material, and plastic material, wherein said solid material is deposited on said substrate. The present invention further provides security ink comprising one or more hydrophilic polymers and a mixture of various photochromic materials.
• US7638073B2
  申请人：——

  公开号：US7638073B2

  公开（公告）日：2009-12-29