2.6-Dimethoxy-4-(2t-nitro-vinyl-(1r))-phenol | 70622-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2.6-Dimethoxy-4-(2t-nitro-vinyl-(1r))-phenol
• 英文别名: ω-Nitro-4-oxy-3.5-dimethoxy-styrol；1²-Nitro-4-oxy-3.5-dimethoxy-1-vinyl-benzol；2,6-Dimethoxy-4-(2-nitro-vinyl)-phenol；2,6-Dimethoxy-4-(2-nitroethenyl)phenol；2,6-dimethoxy-4-[(E)-2-nitroethenyl]phenol
• CAS: 70622-87-6
• 化学式: C₁₀H₁₁NO₅
• 分子量: 225.201
• InChiKey: IVLRLGAGRSQAIN-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2.6-Dimethoxy-4-(2t-nitro-vinyl-(1r))-phenol 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 4-(2-氨基乙基)-2,6-二甲氧基苯酚
  参考文献：
  名称：

  Synthesis of 4-Hydroxy- and 4-Ethoxy-3,5-dimethoxy-β-phenethylamines¹

  摘要：

  DOI：

  10.1021/ja01650a084
• 作为产物：
  描述：

  硝基甲烷 、 丁香醛 在 ammonium acetate 、 溶剂黄146 作用下， 生成 2.6-Dimethoxy-4-(2t-nitro-vinyl-(1r))-phenol
  参考文献：
  名称：

  E-Combretastatin and E-resveratrol structural modifications: Antimicrobial and cancer cell growth inhibitory β-E-nitrostyrenes

  摘要：

  As part of a broad-based SAR investigation of E-resveratrol (strong sirtuin activator and antineoplastic) and the anticancer vascular-targeting combretastatin-type stilbenes, a series of twenty-three beta-E-nitrostyrenes was synthesized in order to evaluate potential antineoplastic, antitubulin, and antimicrobial activities. The beta-E-nitrostyrenes evaluated ranged from monosubstituted phenols to trimethoxy and 3-methoxy- 4,5-methylenedioxy derivatives. Two of the beta-nitrostyrenes were synthesized as water-soluble sodium phosphate derivatives (4t, 4v). All except four (4r, 4s, 4t, 4u) of the series significantly inhibited a minipanel of human cancer cell lines. All but eight led to an IC50 of < 10 mu M for inhibition of tubulin polymerization, and all except three (4l, 4t, 4v) displayed antimicrobial activity. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.07.076

文献信息

• Mauthner, Journal fur praktische Chemie (Leipzig 1954), 1915, vol. <2> 92, p. 200
  作者：Mauthner

  DOI：——

  日期：——
• EP0007372A1
  申请人：——

  公开号：EP0007372A1

  公开（公告）日：1980-02-06
• US4318986A
  申请人：——

  公开号：US4318986A

  公开（公告）日：1982-03-09
• [EN] ENZYME ASSAYS
  申请人：——

  公开号：WO1979000255A1

  公开（公告）日：1979-05-17

  (EN) An enzyme assay reagent comprises a substance which is capable of interaction with the enzyme to give rise to the formation of a compound of formula X-A-Y-NO2, wherein A comprises an aromatic nucleus, X comprises an auxochromic group and Y comprises a unsaturated group which is capable of transmitting electron resonance between the aromatic nucleus and the nitro substituent, said compound per se being capable of producing a visual signal which is easily discernible by eye. The reagent may be used in a through-flow device comprising an upper incubation compartment (1) and a lower visualisation compartment (2) held together by pivot pin (11); the lower compartment contains a quantity of fibrous cellulose (3) sandwiched between upper (4) and lower (5) layers of cotton wool. (FR) Un reactif d"essai d"enzymes comprend une substance capable de reagir avec l"enzyme pour donner lieu a la formation d"un compose de formule X-A-Y-NO2, ou A comprend un noyau aromatique, X comprend un groupe auxochromique et Y comprend un groupe insature capable de transmettre la resonance d"electrons entre le noyau aromatique et le substituant nitro, ledit compose per se etant capable de produire un signal visuel facilement perceptible a l"oeil.
• E-Combretastatin and E-resveratrol structural modifications: Antimicrobial and cancer cell growth inhibitory β-E-nitrostyrenes
  作者：Robin K. Pettit、George R. Pettit、Ernest Hamel、Fiona Hogan、Bryan R. Moser、Sonja Wolf、Sandy Pon、Jean-Charles Chapuis、Jean M. Schmidt

  DOI：10.1016/j.bmc.2009.07.076

  日期：2009.9

  As part of a broad-based SAR investigation of E-resveratrol (strong sirtuin activator and antineoplastic) and the anticancer vascular-targeting combretastatin-type stilbenes, a series of twenty-three beta-E-nitrostyrenes was synthesized in order to evaluate potential antineoplastic, antitubulin, and antimicrobial activities. The beta-E-nitrostyrenes evaluated ranged from monosubstituted phenols to trimethoxy and 3-methoxy- 4,5-methylenedioxy derivatives. Two of the beta-nitrostyrenes were synthesized as water-soluble sodium phosphate derivatives (4t, 4v). All except four (4r, 4s, 4t, 4u) of the series significantly inhibited a minipanel of human cancer cell lines. All but eight led to an IC50 of < 10 mu M for inhibition of tubulin polymerization, and all except three (4l, 4t, 4v) displayed antimicrobial activity. (C) 2009 Published by Elsevier Ltd.