4-{2-[(2-hydroxy-benzylidene)-amino]-ethyl}-phenol | 73428-20-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-{2-[(2-hydroxy-benzylidene)-amino]-ethyl}-phenol
• 英文别名: {2-[(E)-2-(4-hydroxyphenylethyl)iminomethyl]phenol}；2-[(E)-2-(4-hydroxyphenyl)ethyliminomethyl]phenol；(E)-2-((4-hydroxyphenethylimino)methyl)phenol；4-(2-salicylidenamino-ethyl)-phenol；N-Salicylal-4-oxy-β-phenaethylamin；4-(2-Salicylidenamino-aethyl)-phenol
• CAS: 73428-20-3
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: OYJQUNLGKYOYQL-LFIBNONCSA-N

物化性质

• 沸点：
  435.9±35.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  18.0
• 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：
  52.82
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-{2-[(2-hydroxy-benzylidene)-amino]-ethyl}-phenol 在 sodium tetrahydroborate 、 sodium tetraborate decahydrate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 56.0h， 生成 4',4',6',6'-tetra{1-[4-(2-aminoethyl)pyrrolidinyl]}-3,4-dihydro-3-(4-hydroxyphenylethyl)-3H,4H-spiro{[1,3,2-benzoxazaphosphinine]-2,2'-[1,3,5,2,4,6]triazatriphosphinine}
  参考文献：
  名称：

  spiro -Cyclotriphosphazenes containing 4-hydroxyphenylethyl pendant arm: Syntheses, structural characterization and DNA interaction study

  摘要：

  The reaction of hexachlorocyclotriphosphazene, N3P3Cl6, with tyramine podand (2) afforded partly substituted spiro-cyclotriphosphazene (3). Amine-substituted spiro-cyclotriphosphazenes 4a-g were prepared by substitution of the Cl-atoms in 3 with pyrrolidine, piperidine, morpholine, 1,4-dioxa-8-azaspiro[4,5]decane, 1-(2-aminoethyl)pyrrolidine, 1-(2-aminoethyl) piperidine, and 4-(2-aminoethyl)-morpholine, respectively. All of the cyclotriphosphazene derivatives were characterized by elemental analysis, FTIR, MS, 1D H-1, C-13 and P-31 NMR and 2D HSQC techniques, and the crystal structures of 3 and 4b were verified by X-ray diffraction analysis. The relationships delta P-OPN shifts with exocyclic OPN (alpha') and endocyclic NPN (alpha) bond angles, and electron density transfer parameters Delta(P-N) for spiro-cyclotriphosphazenes were presented. The DNA cleavage activity of cyclotriphosphazene derivatives (3, and 4a-g) was studied on double-stranded pBR322 DNA using gel electrophoresis experiments. It was found that 4e and 4f caused the highest level of DNA damage. The interactions of 3 and 4e with calf thymus DNA were also investigated using absorption spectrometry. The molecular docking was performed to identify the interaction of the compounds (3 and 4b) with the DNA (PDB ID:3V9D for A-DNA and PDB ID:1BNA for B-DNA). (C) 2018 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2018.01.016
• 作为产物：
  描述：

  对羟基苯乙胺 、 水杨醛 以 甲醇 为溶剂， 生成 4-{2-[(2-hydroxy-benzylidene)-amino]-ethyl}-phenol
  参考文献：
  名称：

  spiro -Cyclotriphosphazenes containing 4-hydroxyphenylethyl pendant arm: Syntheses, structural characterization and DNA interaction study

  摘要：

  The reaction of hexachlorocyclotriphosphazene, N3P3Cl6, with tyramine podand (2) afforded partly substituted spiro-cyclotriphosphazene (3). Amine-substituted spiro-cyclotriphosphazenes 4a-g were prepared by substitution of the Cl-atoms in 3 with pyrrolidine, piperidine, morpholine, 1,4-dioxa-8-azaspiro[4,5]decane, 1-(2-aminoethyl)pyrrolidine, 1-(2-aminoethyl) piperidine, and 4-(2-aminoethyl)-morpholine, respectively. All of the cyclotriphosphazene derivatives were characterized by elemental analysis, FTIR, MS, 1D H-1, C-13 and P-31 NMR and 2D HSQC techniques, and the crystal structures of 3 and 4b were verified by X-ray diffraction analysis. The relationships delta P-OPN shifts with exocyclic OPN (alpha') and endocyclic NPN (alpha) bond angles, and electron density transfer parameters Delta(P-N) for spiro-cyclotriphosphazenes were presented. The DNA cleavage activity of cyclotriphosphazene derivatives (3, and 4a-g) was studied on double-stranded pBR322 DNA using gel electrophoresis experiments. It was found that 4e and 4f caused the highest level of DNA damage. The interactions of 3 and 4e with calf thymus DNA were also investigated using absorption spectrometry. The molecular docking was performed to identify the interaction of the compounds (3 and 4b) with the DNA (PDB ID:3V9D for A-DNA and PDB ID:1BNA for B-DNA). (C) 2018 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2018.01.016

文献信息

• ABSCISIC ACID BIOSYNTHESIS INHIBITOR
  申请人：Riken

  公开号：EP1439165A1

  公开（公告）日：2004-07-21

  Compounds represented by the following general formula (I) or salts thereof: wherein R1 represents hydrogen atom, hydroxyl group, or an alkoxy group; R2 represents hydroxyl group or an alkoxy group which may be substituted; R3 represents hydrogen atom or an alkyl group which may be substituted; Y represents -CH=CH- or -CH2-; n represents 0 or 1; Ar represents an aryl group which may be substituted or a heteroaryl group which may be substituted, which are useful as inhibitors against the abscisic acid biosynthesis and plant growth regulators.

  由以下通式(I)代表的化合物或其盐： 其中 R1 代表氢原子、羟基或烷氧基；R2 代表羟基或可被取代的烷氧基；R3 代表氢原子或可被取代的烷基；Y 代表 -CH=CH- 或 -CH2-；n 代表 0 或 1；Ar 代表可被取代的芳基或可被取代的杂芳基，可用作赤霉酸生物合成抑制剂和植物生长调节剂。
• Abscisic acid biosynthesis inhibitor
  申请人：Yoshida Shigeo

  公开号：US20050014651A1

  公开（公告）日：2005-01-20

  Compounds represented by the following general formula (I) or salts thereof: wherein R 1 represents hydrogen atom, hydroxyl group, or an alkoxy group; R 2 represents hydroxyl group or an alkoxy group which may be substituted; R 3 represents hydrogen atom or an alkyl group which may be substituted; Y represents —CH═CH— or —CH 2 —; n represents 0 or 1; Ar represents an aryl group which may be substituted or a heteroaryl group which may be substituted, which are useful as inhibitors against the abscisic acid biosynthesis and plant growth regulators.

  以下通式 (I) 所代表的化合物或其盐类： 其中 R 1 代表氢原子、羟基或烷氧基； R 2 代表羟基或可被取代的烷氧基； R 3 代表氢原子或可被取代的烷基； Y 代表 -CH═CH- 或 -CH 2 -Ar 代表可被取代的芳基或可被取代的杂芳基，可用作赤霉酸生物合成抑制剂和植物生长调节剂。
• Inhibitor against biosynthesis of abscisic acid
  申请人：Yoshida Shigeo

  公开号：US20060148650A1

  公开（公告）日：2006-07-06

  Compounds represented by the following general formula (I) or salts thereof: wherein R 1 represents hydrogen atom, hydroxyl group, or an alkoxy group; R 2 represents hydroxyl group or an alkoxy group which may be substituted; R 3 represents hydrogen atom or an alkyl group which may be substituted; Y represents —CH═CH— or —CH 2 —; n represents 0 or 1; Ar represents an aryl group which may be substituted or a heteroaryl group which may be substituted, which are useful as inhibitors against the abscisic acid biosynthesis and plant growth regulators.

  以下通式 (I) 所代表的化合物或其盐类： 其中 R 1 代表氢原子、羟基或烷氧基； R 2 代表羟基或可被取代的烷氧基； R 3 代表氢原子或可被取代的烷基； Y 代表 -CH═CH- 或 -CH 2 -Ar 代表可被取代的芳基或可被取代的杂芳基，可用作赤霉酸生物合成抑制剂和植物生长调节剂。
• 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.
• A new lead compound for abscisic acid biosynthesis inhibitors targeting 9-cis-epoxycarotenoid dioxygenase
  作者：Sun-young Han、Nobutaka Kitahata、Tamio Saito、Masatomo Kobayashi、Kazuo Shinozaki、Shigeo Yoshida、Tadao Asami

  DOI：10.1016/j.bmcl.2004.04.035

  日期：2004.6

  9-cis-Epoxycarotenoid dioxygenase (NCED), a key enzyme in abscisic acid (ABA) biosynthesis, cleaves the olefinic double bond of 9-cis-epoxycarotenoid. Several analogues of nordihydroguaiaretic acid (NDGA) were designed and synthesized, and their efficacy as inhibitors of NCED was examined. One of the synthesized compounds (20) was found to be an inhibitor of this enzyme, and inhibited ABA accumulation and stomatal closing, suggesting that 20 should be ABA biosynthesis inhibitor. (C) 2004 Elsevier Ltd. All rights reserved.