salicylaldehyde tryptophan | 83001-63-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: salicylaldehyde tryptophan
• 英文别名: 2-((2-hydroxybenzylidene)amino)-3-(1H-indol-3-yl)propanoic acid；salicylidene tryptophan；salicylidene-L-tryptophan；(2S)-2-[(2-hydroxyphenyl)methylideneamino]-3-(1H-indol-3-yl)propanoic acid
• CAS: 83001-63-2
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: MIZUBYQJARPJDC-INIZCTEOSA-N

物化性质

• 熔点：
  >200 °C (decomp)(Solv: methanol (67-56-1))
• 沸点：
  558.9±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  85.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二正丁基氧化锡 、 salicylaldehyde tryptophan 以 苯 为溶剂， 以84%的产率得到[(n-butyl)2Sn(salicylidene-L-tryptophan)]
  参考文献：
  名称：

  Synthesis and structural characterization of diorganotin(IV) esters of salicylidene-amino acids

  摘要：

  Eight diorganotin esters of salicylidene-L-tryptophan(Sal-T) and salicylidene-L-valine(Sal-V), [(n-Bu)(2)Sn(Sal-T)] (1), [(n-Bu)(2)Sn(Sal-V)] (2), [Ph2Sn(Sal-T)] (3), [Ph2Sn(Sal-V)] (4), [(PhCH2)(2)Sn(Sal-T)] (5), [(PhCH2)(2)Sn(Sal-V)] (6), [(4-ClC6H4CH2)(2)Sn(Sal-T)] (7) and [(4-ClC6H4CH2)(2)Sn(Sal-V)] (8) have been synthesized and characterized by elemental analysis, IR and H-1 NMR. The crystal structures of compounds 1 and 2 have been determined by X-ray single crystal diffraction. Their structures show the tin atoms of two compounds are rendered five-coordinated in distorted trigonal bipyramidal geometries. (C) 2004 Published by Elsevier B.V.

  DOI：

  10.1016/j.jorganchem.2004.05.004
• 作为产物：
  描述：

  水杨醛 、 L-色氨酸 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 salicylaldehyde tryptophan
  参考文献：
  名称：

  六种 L-色氨酸席夫碱铜 (II) 配合物作为有前途的体外抗癌剂的合成和生物学评价

  摘要：

  六种铜(II)配合物，[Cu(sal-trp)(phen)]·0.5H 2 O·0.5CH 2 Cl 2 ·CH 3 OH ( 1 ), Cu( o -van-trp)(phen) ( 2 )、[Cu(naph-trp)(phen)]·H 2 O ( 3 )、Cu(sal-trp)(bipy) ( 4 )、Cu( o -van-trp)(bipy) ( 5 ) 和 Cu (naph-trp)(bipy) ( 6 ) [sal = 水杨醛；trp = L-色氨酸；phen = 1,10-菲咯啉；o -van =  o -vanllin; 萘 = 2-羟基-1-萘醛；bipy = 2, 2'-联吡啶]，已被合成和表征。复合物之间的比较结合谱通过各种光谱技术、粘度和热变性测量研究了1∼6和小牛胸腺 DNA (CT-DNA)。此外，计算的K b、 K sq和ΔT m值用于量化复合物 1~6 与 CT-DNA

  DOI：

  10.1016/j.molstruc.2022.132578

文献信息

• ROS dependent antitumour activity of photo-activated iron(III) complexes of amino acids
  作者：S Binita Chanu、MD Kausar Raza、Samya Banerjee、Pooja Rani Mina、Dulal Musib、Mithun Roy

  DOI：10.1007/s12039-018-1584-3

  日期：2019.2

  cells was responsible for apoptotic cell death. Decarboxylation or phenolate-Fe(III) charge transfer of photo-activated iron(III) complexes generating \(^\bullet }\)OH radicals (ROS) were responsible for the apoptosis. Overall, the tumour-selective photo-activated anticancer activity of the amino acid-based iron(III) complexes have shown a promising aspect in developing iron-based photo-chemotherapeutics

  摘要通式\（[\ hbox Fe（L）} _ 2}] ^ -} \）的几种基于氨基酸的光敏单体铁（III）配合物，其中\（\ hbox L} =）合成席夫碱配体（水杨烯精氨酸，水杨基内酯色氨酸，3,5-二叔丁基联苯丙氨酸精氨酸和水杨基色氨酸），表征并探索其对常肝细胞，HeLa和MCF-7细胞的光活化抗癌活性。配合物表现出显着的光细胞毒性，其\（\ hbox IC} _ 50}} \）值达到\（0.7 \，\ upmu \ hbox M} \）在可见光下对Chang Liver Cells有抑制作用，与​​在黑暗中的细胞毒性相比，其细胞毒性增强了40倍。配合物在黑暗和可见光是非毒性的MCF-10A（正常细胞）（\（\ hbox中IC} _ 50}> 100 \，\ upmu \ hbox中M} \）在黑暗; \（\ hbox中IC} _ 50}> 80 \，\ upmu
• Synthesis, characterization, density functional theory studies and antibacterial activity of a new Schiff base dioxomolybdenum(VI) complex with tryptophan as epoxidation catalyst
  作者：Zeinab Asgharpour、Faezeh Farzaneh、Mina Ghiasi、Mohammad Azarkish

  DOI：10.1002/aoc.3782

  日期：2017.11

  theory for studying the molecular structure. An in vitro antibacterial activity evaluation showed that [MoO2(Sal‐Tryp)EtOH] complex exhibits good inhibitory effects against Gram‐positive (Bacillus subtilis, Staphylococcus aureus) and Gram‐negative (Escherichia coli, Pseudomonas aeruginosa) bacteria in comparison to standard antibacterial drugs. It was also found that [MoO2(Sal‐Tryp)EtOH] complex successfully

  甲顺-dioxomolybdenum（VI）复合物用制备的MoO 2（乙酰丙酮）2和席夫碱配体（2 - （（2-羟基苯亚甲基）氨基）-3-（1- ħ -吲哚-3-基）丙酸）衍生从水杨醛和升乙醇-色氨酸和指定为[的MoO 2（SAL-的Tryp）（EtOH）中]。它使用多种技术进行了表征，包括热重分析和元素分析以及质量，傅立叶变换红外光谱和紫外可见光谱。使用密度泛函理论进行理论计算以研究分子结构。的体外抗菌活性评估表明，[的MoO 2与标准抗菌药物相比，（SAl-Tryp）EtOH]复合物对革兰氏阳性菌（枯草芽孢杆菌，金黄色葡萄球菌）和革兰氏阴性菌（大肠杆菌，铜绿假单胞菌）表现出良好的抑制作用。还发现[MoO 2（SAl-Tryp）EtOH]络合物成功地催化了环辛烯，降冰片烯，环己烯，苯乙烯，α-甲基苯乙烯和反式二苯乙烯的环氧化，其转化率为45-100％，选择性为64-100％。根据获得的结
• Singh, H. L.; Sharma, M.; Gupta, M. K., Bulletin of the Polish Academy of Sciences: Chemistry, 1999, vol. 47, # 2, p. 103 - 110
  作者：Singh, H. L.、Sharma, M.、Gupta, M. K.、Varshney, A. K.

  DOI：——

  日期：——
• Synthesis, structure, DNA binding and cleavage properties of ternary amino acid Schiff base-phen/bipy Cu(II) complexes
  作者：Pulimamidi Rabindra Reddy、Addla Shilpa、Nomula Raju、Pallepogu Raghavaiah

  DOI：10.1016/j.jinorgbio.2011.08.022

  日期：2011.12

  Ternary Cu(II) complexes [Cu(II)(saltrp)(B)] (1,2), (saltrp = salicylidene tryptophan, B= 1,10 phenathroline (1) or 2,2' bipyridine (2)) were synthesized and characterized. Complex 2 was structurally characterized by single crystal X-ray crystallography. The molecular structure shows a distorted square pyramidal coordination geometry (CuN3O2) in which the ONO donor Schiff base is bonded to the Cu(II) in the basal plane. The N,N donor heterocyclic base displays an axial-equatorial binding mode. CT-DNA binding studies revealed that the complexes show good binding propensity (Intrinsic binding constant, K-b = 3.32 x 10(5) M-1 for 1 and K-b = 3.10 x 10(5) M-1 for 2). The catalytic role of these complexes in the oxidative and hydrolytic cleavage of DNA was studied in detail. Complex 1 binds and cleaves DNA more efficiently as compared to 2. From the kinetic experiments, rate constants for the hydrolysis of phosphodiester bond of DNA backbone were determined as 1.94 h(-1) and 1.05 h(-1) for 1 and 2 respectively. It amounts to (2.93-5.41) x 10(7) fold rate enhancement compared to uncatalyzed double stranded DNA, which is impressive as compared to related Cu(II) Schiff base complexes. (C) 2011 Elsevier Inc. All rights reserved.