(E)-4-(2-(benzylideneamino)ethyl)phenol | 87201-83-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-4-(2-(benzylideneamino)ethyl)phenol
• 英文别名: 4-(2-benzylidenamino-ethyl)-phenol；N-Benzal-4-oxy-β-phenaethylamin；4-(2-Benzylidenamino-aethyl)-phenol
• CAS: 87201-83-0
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: MXBLMHZZTHPSFU-FOWTUZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  32.59
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-4-(2-(benzylideneamino)ethyl)phenol 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 25.0 ℃ 、2.0 MPa 条件下， 以93%的产率得到N-benzyltyramine
  参考文献：
  名称：

  The use of a continuous flow-reactor employing a mixed hydrogen–liquid flow stream for the efficient reduction of imines to amines

  摘要：

  在连续流动反应器中，通过催化氢化，利用电化学产生的氢源生成混合氢-液流流，实现了亚胺高产率地还原为胺，并具有优异的化学选择性。

  DOI：

  10.1039/b504854k
• 作为产物：
  描述：

  对羟基苯乙胺 、 苯甲醛 在 3 A molecular sieve 作用下， 生成 (E)-4-(2-(benzylideneamino)ethyl)phenol
  参考文献：
  名称：

  The use of a continuous flow-reactor employing a mixed hydrogen–liquid flow stream for the efficient reduction of imines to amines

  摘要：

  在连续流动反应器中，通过催化氢化，利用电化学产生的氢源生成混合氢-液流流，实现了亚胺高产率地还原为胺，并具有优异的化学选择性。

  DOI：

  10.1039/b504854k

文献信息

• [EN] N-PHENYLALKYL SUBSTITUTED (ALPHA)-AMINO CARBOXAMIDE DERIVATIVES AND PROCESS FOR THEIR PREPARATION
  申请人：FARMITALIA CARLO ERBA S.R.L.

  公开号：WO1990014334A1

  公开（公告）日：1990-11-29

  (EN) N-phenylalkyl substituted $g(a)-amino carboxamide derivatives of formula (I), wherein R is C1-C8 alkyl, C3-C8 cycloalkyl, furyl, thienyl, pyridyl or unsubstituted or substituted phenyl; A is a -(CH2)m- or -(CH2)p-X-(CH2)q- group wherein X is -O-, -S- or -NR4-; R1, R2, R3, R'3, R4, n, m, p and q are as herein defined; and each of R5 and R6 is independently hydrogen or C1-C6 alkyl, and the pharmaceutically acceptable salts thereof, are active on the central nervous system and can be used as anti-epileptic, anti-Parkinson, neuroprotective, antidepressant, antispastic and/or hypnotic agents in mammals.(FR) Ces dérivés correspondent à la formule (I), où R est alkyle C1-C8, cycloalkyle C3-C8, furyle, thiényle, pyridyle ou phényle, substitué ou non; A est un groupe -(CH2)m- ou -(CH2)p-X-(CH2)q-, où X est -O-, -S- ou NR4-; R1, R2, R3, R'3, R4, n, m, p et q ont les significations indiquées dans la description; et R5 et R6 sont chacun, indépendamment l'un de l'autre, hydrogène ou alkyle C1-C6. L'invention porte également sur leurs sels pharmaceutiquement acceptables. Ces dérivés et leurs sels agissent sur le système nerveux central et peuvent servir d'agents anti-épileptiques, anti-Parkinson, neuroprotecteurs, antidépressifs, antispastiques et/ou hypnotiques chez les mammifères.

  N-苯基烷基取代的$g(a)-氨基羧酰胺衍生物的化学式(I)，其中R为C1-C8烷基，C3-C8环烷基，呋喃基，噻吩基，吡啶基或未取代或取代的苯基；A为-(CH2)m-或-( )p-X-( )q-基团，其中X为-O-，-S-或-NR4-；R1，R2，R3，R'3，R4，n，m，p和q如本文所定义；R5和R6各自独立为氢或C1-C6烷基，以及其药学上可接受的盐，在哺乳动物的中枢神经系统中具有活性，可用作抗癫痫、抗帕金森、神经保护、抗抑郁、抗痉挛和/或催眠剂。
• N-phenylalkyl substituted alfa-amino carboxamide derivatives and process for their preparation
  申请人：FARMITALIA CARLO ERBA S.r.l.

  公开号：EP0400495A1

  公开（公告）日：1990-12-05

  N-phenylalkyl substituted α-amino carboxamide derivatives of formula (I) wherein R is C₁-C₈ alkyl, C₃-C₈ cycloalkyl, furyl, thienyl, pyridyl or unsubstituted or substituted phenyl; A is a -(CH₂)m- or -(CH₂)p-X-(CH₂)q- group wherein X is -O-, -S- or -NR₄-; R₁, R₂, R₃, R′₃, R₄, n, m, p and q are as herein defined; and each of R₅ and R₆ is independently hydrogen or C₁-C₆ alkyl, and the pharmaceutically acceptable salts thereof, are active on the central nervous system and can be used as anti-epileptic, anti-Parkinson, neuroprotective, antidepressant, antispastic and/or hypnotic agents in mammals.

  式 (I) 的 N-苯基烷基取代的 α-氨基羧酰胺衍生物 其中 R 是 C₁-C₈ 烷基、C₃-C₈ 环烷基、呋喃基、噻吩基、吡啶基或未取代或取代的苯基； A 是-(CH₂)m-或-(CH₂)p-X-(CH₂)q-基团，其中 X 是-O-、-S-或-NR₄-；R₁、R₂、R₃、R′₃、R₄、n、m、p 和 q 如本文所定义；R₅和 R₆各自独立地为氢或 C₁-C₆烷基，其药学上可接受的盐类对中枢神经系统有活性，可用作哺乳动物的抗癫痫、抗帕金森、神经保护、抗抑郁、解痉剂和/或催眠药。
• Ultrasonic synthesis of tyramine derivatives as novel inhibitors of <b>α</b>-glucosidase <i>in vitro</i>
  作者：Hina Siddiqui、Muhammad Arslan Bashir、Kulsoom Javaid、Arsalan Nizamani、Huma Bano、Sammer Yousuf、Atta-ur Rahman、M. Iqbal Choudhary

  DOI：10.3109/14756366.2016.1142983

  日期：2016.11.1

  Tyramine derivatives 3-27 were synthesized by using conventional and environmental friendly ultrasonic techniques. These derivatives were then evaluated for the first time for their a-glucosidase (Sources: Saccharomyces cerevisiae and mammalian rat-intestinal acetone powder) inhibitory activity by using in vitro mechanism-based biochemical assays. Compounds 7, 14, 20, 21 and 26 were found to be more active (IC50 = 49.7 +/- 0.4, 318.8 +/- 3.7, 23.5 +/- 0.9, 302.0 +/- 7.3 and 230.7 +/- 4.0 mu M, respectively) than the standard drug, acarbose (IC50 = 840.0 +/- 1.73 mu M (observed) and 780 +/- 0.028 mu M (reported)) against alpha-glucosidase obtained from Saccharomyces cerevisiae. Kinetic studies were carried out on the most active members of the series in order to determine their mode of inhibition and dissociation constants. Compounds 7, 20 and 26 were found to be the competitive inhibitors of alpha-glucosidase. These compounds were also screened for their protein antiglycation, and dipeptidyl peptidase-IV (DPP-IV) inhibitory activities. Only compounds 20, 22 and 27 showed weak antiglycation activity with IC50 values 505.27 +/- 5.95, 581.87 +/- 5.50 and 440.58 +/- 2.74 mu M, respectively. All the compounds were found to be inactive against DDP-IV enzyme. Inhibition of alpha-glucosidase, DPP-IV enzymes and glycation of proteins are valid targets for the discovery of antidiabetic drugs. Cytotoxicity of compounds 3-27 was also evaluated by using mouse fibroblast 3T3 cell lines. All the compounds were found to be noncytotoxic. The current study describes the synthesis alpha-glucosidase inhibitory activity of derivatives, based on a natural product tyramine template. The compounds reported here may serve as the starting point for the design and development of novel alpha-glucosidase inhibitors as antidiabetic agents.
• DE259193
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• DE259874
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