(E)-8a-methyl-2-(4-methylbenzylidene)-3,4,8,8a-tetrahydronaphthalene-1,6(2H,7H)-dione | 1289642-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-8a-methyl-2-(4-methylbenzylidene)-3,4,8,8a-tetrahydronaphthalene-1,6(2H,7H)-dione
• 英文别名: (2E)-8a-methyl-2-[(4-methylphenyl)methylidene]-3,4,7,8-tetrahydronaphthalene-1,6-dione
• CAS: 1289642-69-8
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: WVVWWLCHIMCVKY-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-4a'-methyl-6'-(4-methylbenzylidene)-4',4a',7',8'-tetrahydro-3'H-spiro[[1,3]dithiolane-2,2'-naphthalen]-5'(6'H)-one 在 N-氯代丁二酰亚胺 、 silver nitrate 作用下， 以 乙腈 为溶剂， 以93%的产率得到(E)-8a-methyl-2-(4-methylbenzylidene)-3,4,8,8a-tetrahydronaphthalene-1,6(2H,7H)-dione
  参考文献：
  名称：

  Structural requirements of (E)-6-benzylidene-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one derivatives as novel melanogenesis inhibitors

  摘要：

  Chalcone type compound 1a ((E)-6'-benzylidene-4a'-methyl-4',4a',7',8'-tetrahydro-3'H-spiro[[1,3]dithiolane-2,2'-naphthalen]-5'(6'H)-one) was discovered as an potent inhibitor in melanogenesis. To define its structure-activity relationship, a series of analogs 1b-n, dithiolane truncated 2a-b and ring A removed 3a-e were prepared and evaluated. The electron donating substitution on the phenyl ring (ring C) rather than an electron withdrawing group and dithiolane motif of 1 are needed for the activity enhancement. The scaffold containing both rings A and B associated with alpha,beta-unsaturated system connected to phenyl of 1 was essential for antimelanogenesis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.060

文献信息

• Reduced naphthalenes, their preparation and use
  申请人：BEECHAM GROUP PLC

  公开号：EP0045219A1

  公开（公告）日：1982-02-03

  A compound of the formula (I) and pharmaceutically acceptable salts thereof: wherein: Ar is phenyl, optionally substituted by one or more C1-4 alkyl, C1-4 alkoxy, halogen, cyano, nitro, hydroxy, CONH2, C02W wherein W ist C1-6 alkyl of C1-4 alkylphenyl which phenyl may be substituted by one or more C1-4 alkyl, C1-4 alkoxy or halogen, NR1R2 wherein R1 and R2 are selected from hydrogen or C1-6 alkyl, NHCO C1-6 alkyl or C1-6 alkylcarbonyloxy; phenyl disubstituted on adjacent carbon atoms by methylenedioxy; furyl or thienyl; the dotted lines represent an optionally present double bond; and X is CO or CR1OH wherein R1 is hydrogen or C1-4 alkyl, having useful pharmacological activity, processes for their preparation and their use.

  式 (I) 的化合物及其药学上可接受的盐类： 其中 Ar 是苯基，可任选被一个或多个 C1-4 烷基、C1-4 烷氧基、卤素、氰基、硝基、羟基、CONH2、C02W（其中 Wt 是 C1-6 烷基的 C1-4 烷基苯基，苯基可被一个或多个 C1-4 烷基、C1-4 烷氧基或卤素取代）、NR1R2（其中 R1 和 R2 选自氢或 C1-6 烷基、NHCO C1-6 烷基或 C1-6 烷基羰氧基）、在相邻碳原子上被亚甲基二氧基、呋喃基或噻吩基取代的苯基； 虚线代表任选存在的双键；以及 X是CO或CR1OH，其中R1是氢或C1-4烷基。
• US4382094A
  申请人：——

  公开号：US4382094A

  公开（公告）日：1983-05-03
• Structural requirements of (E)-6-benzylidene-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one derivatives as novel melanogenesis inhibitors
  作者：Pillaiyar Thanigaimalai、Ki-Cheul Lee、Vinay K. Sharma、Eeda Vekateswara Rao、Eunmiri Roh、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.bmcl.2011.02.060

  日期：2011.4

  Chalcone type compound 1a ((E)-6'-benzylidene-4a'-methyl-4',4a',7',8'-tetrahydro-3'H-spiro[[1,3]dithiolane-2,2'-naphthalen]-5'(6'H)-one) was discovered as an potent inhibitor in melanogenesis. To define its structure-activity relationship, a series of analogs 1b-n, dithiolane truncated 2a-b and ring A removed 3a-e were prepared and evaluated. The electron donating substitution on the phenyl ring (ring C) rather than an electron withdrawing group and dithiolane motif of 1 are needed for the activity enhancement. The scaffold containing both rings A and B associated with alpha,beta-unsaturated system connected to phenyl of 1 was essential for antimelanogenesis. (C) 2011 Elsevier Ltd. All rights reserved.