丁香醛连氮 | 14414-32-5

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 丁香醛连氮
• 中文别名: 丁香醛联氮；3,5-二甲氧基-4-羟基苯甲醛连氮
• 英文名称: syringaldazine
• 英文别名: 4-hydroxy-3,5-dimethoxybenzaldehyde azine；SGZ；Syringaldazin；4-[[(4-hydroxy-3,5-dimethoxyphenyl)methylidenehydrazinylidene]methyl]-2,6-dimethoxyphenol
• CAS: 14414-32-5
• 化学式: C₁₈H₂₀N₂O₆
• mdl: MFCD00008363
• 分子量: 360.367
• InChiKey: YARKTHNUMGKMGS-UHFFFAOYSA-N

物化性质

• 熔点：
  209-210 °C (lit.)
• 沸点：
  492.4°C (rough estimate)
• 密度：
  1.3595 (rough estimate)
• 溶解度：
  DMF：微浊
• LogP：
  0.553 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 安全说明：
  S26,S36
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 包装等级：
  III
• 危险类别：
  4.1
• 危险品运输编号：
  1325

反应信息

• 作为反应物：
  描述：

  丁香醛连氮 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 氯化亚砜 、 palladium 10% on activated carbon 、 水 、 氢气 、 sodium methylate 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 20.0 ℃ 、405.33 kPa 条件下， 反应 11.0h， 生成 3,5-dimethoxy-4-hydroxybibenzyl
  参考文献：
  名称：

  Design, synthesis and antitumour and anti-angiogenesis evaluation of 22 moscatilin derivatives

  摘要：

  Two series of moscatilin derivatives were designed, synthesized and evaluated as anti-tumor and anti-angiogenesis agents. Most of these compounds showed moderate-to-obvious cytotoxicity against five cancer cell lines (A549, HepG2, MDA-MB-231, MKN-45, HCT116). Among these cell lines, compounds had obvious effects on HCT116. Especially for 8Ae, the IC50 was low to 0.25 mu M. 8Ae can inhibit the viability and induce the apoptosis of HCT116 cells but exhibit no cytotoxic activity in noncancerous NCM460 colon cells. 8Ae can also arrest the G2/M cell cycle in HCT116 cells by inhibiting the alpha-tubulin expression. Zebrafish bioassay-guided screen showed the 22 moscatilin derivatives had potent anti-angiogenic activities and compound 8Ae had better activities than positive compound. Molecular docking indicated 8Ae interacted with tubulin at the affinity of -7.2 Kcal/mol. In conclusion, compound 8Ae was a potential antitumor and anti-angiogenesis candidate for further development.

  DOI：

  10.1016/j.bmc.2019.04.027
• 作为产物：
  描述：

  丁香醛 在 肼 作用下， 生成 丁香醛连氮
  参考文献：
  名称：

  Saint-Ruf,G.; Buu-Hoi,N.P., Bulletin de la Societe Chimique de France, 1970, p. 525 - 527

  摘要：

  DOI：
• 作为试剂：
  描述：

  还原型辅酶Ⅰ 在 丁香醛连氮 、 Didymocrea sp. laccase 、 氧气 作用下， 以 aq. buffer 为溶剂， 生成 nicotinamide adenine dinucleotide
  参考文献：
  名称：

  Development of a laccase/syringaldazine system for NAD(P)H oxidation

  摘要：

  The kinetics of laccase-catalyzed NAD(P)H oxidation in the presence of syringaldazine (4-hydroxy3,5-dimethoxybenzaldehyde azine) was investigated spectrophotometrically and by measuring the consumption of oxygen. Laccases from Didymocrea sp. (DsL) and Trichaptum abietinum (TaL) were used. These enzymes showed different pH profiles towards syringaldazine. DsL showed a maximum activity at pH 8.0 that is unusual for fungal laccases. The maximal activity of TaL was observed at pH 5.5. A kinetic mechanism for the laccase-catalyzed syringaldazine oxidation and disproportionation of reaction products as well as their reaction with NAD(P)H was suggested. Since TaL was slightly more reactive with syringaldazine than DsL, the calculated constants of enzymatic reaction were different for the investigated laccases. The constant of NAD(P)H oxidation by oxidized syringaldazine (tetramethoxy azobismethylene quinine, TMAMQ) is 1.0 x 10(4) M-1 S-1, which was sufficient for effective NAD(P)H oxidation. The production of an enzymatically active NAD(+) was proved by coupling the laccase/mediator system with alcohol oxidation catalyzed by yeast alcohol dehydrogenase. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.12.013

文献信息

• Syringaldehyde as a scaffold for the synthesis of some biologically potent heterocycles
  作者：Ahmed S. A. Youssef、Magdy M. Hemdan、Mohammad E. Azab、Samir A. Emara、Galal A. Elsayed、Rabaa M. Kamel

  DOI：10.1002/jhet.3850

  日期：2020.3

  Syringaldehyde was utilized in synthesis of different heterocyclic systems. Some of the synthesized compounds 2, 7, 8, 10, 11, and 13 were tested for antioxidant activity where they showed ability to inhibit oxidation in kidney and rat brain homogenates using 2, 2′‐azinobis (3‐ethylbenzothiazoline‐6‐sulfonic acid) (ABTS). Also, the activity against cancer was examined using the standard MTT method

  丁醛用于合成不同的杂环系统。一些合成的化合物2，7，8，10，11，和13分别为抗氧化活性进行测试，他们使用2，2'- azinobis（3-乙基-6-磺酸显示出肾脏和大鼠脑匀浆能力以抑制氧化酸）（ABTS）。另外，使用标准MTT方法针对两种人肿瘤细胞系检测了抗癌活性。乳腺乳腺癌MCF-7和肝细胞癌HepG2。化合物8和11表现出最高的抗氧化剂和抗肿瘤药活性。然而，化合物10和13显示出中等活性。同时，化合物2，7呈弱活动。
• Synthesis of Azines in Solid State: Reactivity of Solid Hydrazine with Aldehydes and Ketones
  作者：Byeongno Lee、Kyu Hyung Lee、Jaeheung Cho、Wonwoo Nam、Nam Hwi Hur

  DOI：10.1021/ol202593g

  日期：2011.12.16

  Highly conjugated azines were prepared by solid state grinding of solid hydrazine and carbonyl compounds such as aldehydes and ketones, using a mortar and a pestle. Complete conversion to the azine product is generally achieved at room temperature within 24 h, without using solvents or additives. The solid-state reactions afford azines as the sole products with greater than 97% yield, producing only water and carbon dioxide as waste.
• Extraction of hemoglobin with calixarenes and biocatalysis in organic media of the complex with pseudoactivity of peroxidase
  作者：Magda C. Semedo、Amin Karmali、Patrícia D. Barata、José V. Prata

  DOI：10.1016/j.molcatb.2009.09.017

  日期：2010.1

  The present work involves the use of p-tert-butylcalix[4,6,8]arene carboxylic acid derivatives ((t)Butyl[4,6,8]CH2COOH) for selective extraction of hemoglobin. All three calixarenes extracted hemoglobin into the organic phase, exhibiting extraction parameters higher than 0.90. Evaluation of the solvent accessible positively charged amino acid side chains of hemoglobin (PDB entry 1XZ2) revealed that there are 8 arginine, 44 lysine and 30 histidine residues on the protein surface which may be involved in the interactions with the calixarene molecules. The hemoglobin-(t)Butyl[6]CH2COOH complex had pseudoperoxidase activity which catalysed the oxidation of syringaldazine in the presence of hydrogen peroxide in organic medium containing chloroform. The effect of pH, protein and substrate concentrations on biocatalysis was investigated using the hemoglobin-(t)Butyl[6]CH2COOH complex. This complex exhibited the highest specific activity of 9.92 x 10(-2) U mg protein(-1) at an initial pH of 7.5 in organic medium. Apparent kinetic parameters (V'(max), K'(m), k'(cat) and k'(cat)/K'(m)) for the pseudoperoxidase activity were determined in organic media for different pH values from a Michaelis-Menten plot. Furthermore, the stability of the protein-calixarene complex was investigated for different initial pH values and half-life (t(1/2)) values were obtained in the range of 1.96 and 2.64 days. Hemoglobin-calixarene complex present in organic medium was recovered in fresh aqueous solutions at alkaline pH, with a recovery of pseudoperoxidase activity of over 100%. These results strongly suggest that the use of calixarene derivatives is an alternative technique for protein extraction and solubilisation in organic media for biocatalysis. (C) 2009 Elsevier B.V. All rights reserved