5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-anthracene-2-carbaldehyde | 161915-38-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-anthracene-2-carbaldehyde
• 英文别名: 5,5,8,8-Tetramethyl-5,6,7,8-tetrahydroanthracene-2-carbaldehyde；5,5,8,8-tetramethyl-6,7-dihydroanthracene-2-carbaldehyde
• CAS: 161915-38-4
• 化学式: C₁₉H₂₂O
• 分子量: 266.383
• InChiKey: IDJHMFAXHIFSNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-anthracene-2-carbaldehyde 在 N-羟基丁二酰亚胺 、 potassium tert-butylate 、 水 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 3-{(Z)-3-Carbamoyl-2-methyl-1-[1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-anthracen-2-yl)-meth-(E)-ylidene]-allyl}-benzamide
  参考文献：
  名称：

  Dicarboxylic acid inhibitors of phospholipase A2

  摘要：

  Ten diacids were synthesized via a simple regio- and stereoselective aldol reaction. All of these compounds were good to excellent inhibitors of 14 kDa human platelet PLA(2), and many of these derivatives displayed activity in a phorbol-ester induced mouse ear edema assay. One of the new compounds reported here was selected for further development as a potential antipsoriasis agent. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00110-8

文献信息

• Alicyclic phospholipase A2 inhibitors
  申请人：Bristol-Myers Company

  公开号：EP0629604A2

  公开（公告）日：1994-12-21

  Compounds of Formula I: wherein the bonds between C₂ and C3 and/or between C₄ and C₅ are unsaturated; X = COOH, H, F, Cl, Br, I, COOR'', CONH₂, COR''', CHO, CH₂OH, CH₂OR''', OH, OR''', CF₃, C1-6 alkyl, C1-6 alkenyl, C1-6 haloalkyl, NO₂, P(O)(OH)₂, SO₂H, or SO₃H; R = substituted or unsubstituted alkyl, aryl, arylalkyl, alkenyl, or arylalkenyl groups, with the proviso that each of these groups must have 6 or more carbons (preferably 6 to 30) and R cannot be R' = H or C1-6 alkyl; R'' = H, C1-6 alkyl, C(R³)₂OC(O)R⁴, CH₂CH₂NR⁵R⁶, CH₂CH₂CH₂NR⁵R⁶, CH₂C(O)N(R⁶)₂, or other groups yielding physiologically hydrolyzable esters; R''' = C1-6 alkyl; R³ = H, CH₃, C₂H₅, CH₃CH₂CH₂ (with R³'s being the same or different); R⁴ = C6-12 aryl, C1-7 linear, branched or cyclic alkyl, or C1-7 linear, branched or cyclic alkoxy; R⁵ = R⁶, or when linked with R⁶, is a C₃-C₆ cycloalkyl or a -CH₂CH₂OCH₂CH₂-group; and R⁶ = C1-3 alkyl; and pharmaceutically-acceptable salts thereof are effective phospholipase A₂ (PLA₂) inhibitors.

  式 I 的化合物： 其中 C₂ 与 C3 之间和/或 C₄ 与 C₅ 之间的键为不饱和键； X = COOH、H、F、Cl、Br、I、COOR''、CONH₂、COR'''、CHO、CH₂OH、CH₂OR'''、OH、OR'''、CF₃、C1-6 烷基、C1-6 烯基、C1-6 卤代烷基、NO₂、P(O)(OH)₂、SO₂H 或 SO₃H； R = 取代或未取代的烷基、芳基、芳烷基、烯基或芳烷烯基，但这些基团都必须具有 6 个或更多的碳原子（最好是 6 至 30 个），且 R 不能是 R' = H 或 C1-6 烷基； R''=H、C1-6 烷基、C(R³)₂OC(O)R⁴、CH₂CH₂NR⁵R⁶、CH₂CH₂CH₂NR⁵R⁶、CH₂C(O)N(R⁶)₂ 或其他可产生生理性水解酯的基团； R''' = C1-6 烷基； R³ = H、CH₃、C₂H₅、CH₃CH₂CH₂（R³'s 相同或不同）； R⁴ = C6-12 芳基，C1-7 直链、支链或环状烷基，或 C1-7 直链、支链或环状烷氧基； R⁵ = R⁶，或当与 R⁶ 连接时，为 C₃-C₆ 环烷基或-CH₂CH₂OCH₂CH₂基团；以及 R⁶ = C1-3 烷基； 及其药学上可接受的盐是有效的磷脂酶 A₂（PLA₂）抑制剂。
• NOUVEAU PROCEDE DE PREPARATION DE DERIVES DU TAXANE, NOUVEAUX DERIVES AINSI OBTENUS ET LES COMPOSITIONS QUI LES CONTIENNENT
  申请人：RHONE-POULENC RORER S.A.

  公开号：EP0669916B1

  公开（公告）日：1997-01-22
• US5436369A
  申请人：——

  公开号：US5436369A

  公开（公告）日：1995-07-25
• Dicarboxylic acid inhibitors of phospholipase A2
  作者：Dane M. Springer、Bing-Yu Luh、Stan V. D'Andrea、Joanne J. Bronson、Muzammil M. Mansuri、James R. Burke、Kurt R. Gregor、Paul L. Stanley、Kenneth M. Tramposch

  DOI：10.1016/s0960-894x(97)00110-8

  日期：1997.1

  Ten diacids were synthesized via a simple regio- and stereoselective aldol reaction. All of these compounds were good to excellent inhibitors of 14 kDa human platelet PLA(2), and many of these derivatives displayed activity in a phorbol-ester induced mouse ear edema assay. One of the new compounds reported here was selected for further development as a potential antipsoriasis agent. (C) 1997 Elsevier Science Ltd.