(E)-N-cyclohexyl-3-(4-hydroxyphenyl)acrylamide | 99564-58-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-N-cyclohexyl-3-(4-hydroxyphenyl)acrylamide
• 英文别名: (E)-N-cyclohexyl-3-(4-hydroxyphenyl)prop-2-enamide
• CAS: 99564-58-6
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: UYEKGCPLNBQNSM-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-N-cyclohexyl-3-(4-hydroxyphenyl)acrylamide 、 methyl 2,3,4-tri-O-benzyl-6-O-(3,4-di-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 碳酸氢钠 作用下， 生成 methyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-O-(3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1-2)-O-[(2,3,4-tetra-O-acetyl-β-D-galactopyranosyl)-(1-4)-O-(3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1-..)]
  参考文献：
  名称：

  Synthesis of tumor-associated saccharides via O-glycosyl trichloroacetic

  摘要：

  The trichloroacetic method was employed to synthesize di- and hexa-saccharides. O-glycosyl trichloroacetic, a stable and readily obtained intermediate, was activated to give a highly reactive glycosyl donor upon treatment with acid and coupled with the acceptor to afford complex glycosides with high stereoselectivity and in good yield. Two free hexasaccharides will be used to explore the possible prevention of metastatic spread. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00373-4
• 作为产物：
  描述：

  反式-4-乙酰氧基肉桂酸 在 4-二甲氨基吡啶 、 氯化亚砜 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 (E)-N-cyclohexyl-3-(4-hydroxyphenyl)acrylamide
  参考文献：
  名称：

  pH-Sensitive exciton chirality chromophore. Solvatochromic effects on circular dichroism spectra

  摘要：

  Diesters (1 and 3) of (1S,2S) and (1R,2R)-cyolohexanediol and diamides (2 and 4) of(1S,2S) and (1R,2R)-diaminocyclohexane with p-hydroxycinnamic acid exhibit intense bisignate circular dichroism spectra in CH3OH: 1 Delta epsilon+55 (323 nm), -34 (287 nm); 2 Delta epsilon+75 (318 nm), -55 (281 nm) and in (CH3)(2)SO: 1 Delta epsilon+53 (328 nm), -33 (292 nm); 2 Delta epsilon+65 (319 nm), -50 (280 nm). Added NaOH causes a bathochromic shift of similar to 50 nm in CH3OH and similar to 80-90 nm in (CH3)(2)SO. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00372-2

文献信息

• Tyrosinase inhibition and anti-melanin generation effect of cinnamamide analogues
  作者：Sultan Ullah、Chaeun Park、Muhammad Ikram、Dongwan Kang、Sanggwon Lee、Jungho Yang、Yujin Park、Sik Yoon、Pusoon Chun、Hyung Ryong Moon

  DOI：10.1016/j.bioorg.2019.03.001

  日期：2019.6

  Abnormal melanogenesis results in excessive production of melanin, leading to pigmentation disorders. As a key and rate-limiting enzyme for melanogenesis, tyrosinase has been considered an important target for developing therapeutic agents of pigment disorders. Despite having an (E)-beta-phenyl-alpha,beta-unsaturated carbonyl scaffold, which plays an important role in the potent inhibition of tyrosinase activity, cinnamic acids have not attracted attention as potential tyrosinase inhibitors, due to their low tyrosinase inhibitory activity and relatively high hydrophilicity. Given that cinnamic acids' structure intrinsically features this (E)-scaffold and following our experience that minute changes in the chemical structure can powerfully affect tyrosinase activity, twenty less hydrophilic cinnamamide derivatives were designed as potential tyrosinase inhibitors and synthesised using a Horner-Wadsworth-Emmons reaction. Four of these cinnmamides (4, 9, 14, and 19) exhibited much stronger mushroom tyrosinase inhibition (over 90% inhibition) at 25 mu M compared to kojic acid (20.57% inhibition); crucially, all four have a 2,4-dihydroxy group on the beta-phenyl ring of the scaffold. A docking simulation using tyrosinase indicated that the four cinnamamides exceeded the binding affinity of kojic acid, and bound more strongly to the active site of tyrosinase. Based on the strength of their tyrosinase inhibition, these four cinnamamides were further evaluated in B16F10 melanoma cells. All four cinnamamides, without cytotoxicity, exhibited higher tyrosinase inhibitory activity (67.33 - 79.67% inhibition) at 25 mu M than kojic acid (38.11% inhibition), with the following increasing inhibitory order: morpholino (9) = cyclopentylamino (14) < cyclohexylamino (19) < N-methylpiperazino (4) cinnamamides. Analysis of tyrosinase activity and melanin content in B16F10 cells showed that the four cinnamamides dose-dependently inhibited both cellular tyrosinase activity and melanin content and that their inhibitory activity at 25 mu M was much better than that of kojic acid. The results of melanin content analysis well matched those of the cellular tyrosinase activity analysis, indicating that tyrosinase inhibition by the four cinnamamides is a major factor in the reduction of melanin production. These results imply that these four cinnamamides with a 2,4-dihydroxyphenyl group can act as excellent anti-melanogenic agents in the treatment of pigmentation disorders.
• pH-Sensitive exciton chirality chromophore. Solvatochromic effects on circular dichroism spectra
  作者：Stefan E. Boiadjiev、David A. Lightner

  DOI：10.1016/0957-4166(96)00372-2

  日期：1996.10

  Diesters (1 and 3) of (1S,2S) and (1R,2R)-cyolohexanediol and diamides (2 and 4) of(1S,2S) and (1R,2R)-diaminocyclohexane with p-hydroxycinnamic acid exhibit intense bisignate circular dichroism spectra in CH3OH: 1 Delta epsilon+55 (323 nm), -34 (287 nm); 2 Delta epsilon+75 (318 nm), -55 (281 nm) and in (CH3)(2)SO: 1 Delta epsilon+53 (328 nm), -33 (292 nm); 2 Delta epsilon+65 (319 nm), -50 (280 nm). Added NaOH causes a bathochromic shift of similar to 50 nm in CH3OH and similar to 80-90 nm in (CH3)(2)SO. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis of tumor-associated saccharides via O-glycosyl trichloroacetic
  作者：Xiao-Xiang Zhu、Ping Yu Ding、Meng-Shen Cai

  DOI：10.1016/0957-4166(96)00373-4

  日期：1996.10

  The trichloroacetic method was employed to synthesize di- and hexa-saccharides. O-glycosyl trichloroacetic, a stable and readily obtained intermediate, was activated to give a highly reactive glycosyl donor upon treatment with acid and coupled with the acceptor to afford complex glycosides with high stereoselectivity and in good yield. Two free hexasaccharides will be used to explore the possible prevention of metastatic spread. Copyright (C) 1996 Published by Elsevier Science Ltd