6-hydroxy-2,5,7,8-tetramethylchromane-2-carbohydrazide | 223723-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-hydroxy-2,5,7,8-tetramethylchromane-2-carbohydrazide
• 英文别名: 6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-2-carbohydrazide；3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-benzopyran-2-carbohydrazide；chromanol；Trolox hydrazide；6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromene-2-carbohydrazide
• CAS: 223723-47-5
• 化学式: C₁₄H₂₀N₂O₃
• 分子量: 264.324
• InChiKey: HXFUAJPFFACBFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  505.7±50.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-hydroxy-2,5,7,8-tetramethylchromane-2-carbohydrazide 在 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 24.0h， 生成 2-[5-(3-chlorobenzylsulfanyl)-[1,3,4]oxadiazol-2-yl]-2,5,7,8-tetramethylchroman-6-ol
  参考文献：
  名称：

  Kumar, Piyush; Rahman, Azizur; Wal, Pranay, Indian Journal of Heterocyclic Chemistry, 2020, vol. 30, # 3, p. 395 - 402

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基氢醌 在 一水合肼 、 二正丁胺 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 30.0h， 生成 6-hydroxy-2,5,7,8-tetramethylchromane-2-carbohydrazide
  参考文献：
  名称：

  Rawat, Pinki; Verma, Saurabh Manaswita; Kumar, Piyush, Indian Journal of Heterocyclic Chemistry, 2020, vol. 30, # 4, p. 515 - 520

  摘要：

  DOI：

文献信息

• Synthesis of conjugates of lupane triterpenoids with chromane antioxidants and in vitro study of their influence on the production of nitrogen monoxide and on the arginase activity in activated macrophages
  作者：A. Yu. Spivak、R. R. Khalitova、Yu. P. Bel’skii、A. N. Ivanova、E. R. Shakurova、N. V. Bel’skaya、V. N. Odinokov、M. G. Danilets、A. A. Ligacheva

  DOI：10.1007/s11172-010-0382-y

  日期：2010.12

  Conjugates of lupane triterpenoids (betulin and betulonic and betulinic acids) with synthetic analogs of α-tocopherol were obtained via ester bond formation and tested in vitro. Showing low cytotoxicity, some of them suppress nitrogen monoxide production without affecting the activity of arginase, which suggests their antiinflammatory and immunomodulating properties.

  通过酯键结合，获得了与α-生育酚合成类似物偶联的白桦三萜（白桦脂醇、白桦脂酮酸和白桦脂酸）衍生物，并在体外进行了测试。结果显示，尽管其细胞毒性较低，但其中一些能够抑制一氧化氮的生成，而不影响精氨酸酶的活性，这表明它们具有抗炎和免疫调节的特性。
• Second generation of α-tocopherol analogs-nitric oxide donors: Synthesis, physicochemical, and biological characterization
  作者：Gloria V. López、Fabiana Blanco、Paola Hernández、Ana Ferreira、Oscar E. Piro、Carlos Batthyány、Mercedes González、Homero Rubbo、Hugo Cerecetto

  DOI：10.1016/j.bmc.2007.06.019

  日期：2007.9

  mimetics with NO-releasing capacity are reported. The selected NO-donor moieties were nitrooxy and furoxan. All products were tested for their in vitro NO-releasing capacities, vasodilating properties and mammal cytotoxic activities. The lipophilic-hydrophilic balance of all products was also evaluated. A new hybrid furoxan, phenol derivative 17, possesses adequate profile of the studied properties.

  报道了一系列具有NO释放能力的α-生育酚模拟物的合成，物理化学和生物学特性。所选的NO供体部分是硝基氧基和呋喃喃。测试了所有产品的体外NO释放能力，血管舒张特性和哺乳动物细胞毒性活性。还评估了所有产品的亲脂-亲水平衡。一种新的杂氧呋喃杂酚衍生物，苯酚衍生物17，具有足够的研究性质。
• Design and synthesis of chroman derivatives with dual anti-breast cancer and antiepileptic activities
  作者：Pinki Rawat、Saurabh M Verma

  DOI：10.2147/dddt.s111266

  日期：——

  anti-breast cancer and antiepileptic activities. All synthesized compounds yielded results that were in good agreement with spectral data. The bioassay showed that some of the resultant compounds exerted remarkable inhibitory effects on growth of human breast cancer cell line MCF-7. In particular, compound 6i (the concentration required for 50% inhibition of cell growth [GI50] =34.7 µM) exerted promising

  设计，制备并检测了一系列苯并二氢吡喃衍生物的抗乳腺癌和抗癫痫活性。所有合成的化合物产生的结果与光谱数据都非常吻合。生物测定法表明，某些所得化合物对人乳腺癌细胞系MCF-7的生长具有显着的抑制作用。特别是，化合物6i（抑制50％细胞生长[GI50] = 34.7 µM所需的浓度）对MCF-7细胞株具有有希望的抗癌活性。另外，化合物6b，6c，6d，6e，6g，6i和6l显示出比参考药物更高的抗癫痫活性。如通过旋转脚踏试验所确定的，没有一种化合物显示出神经毒性。所得结果证明，这些独特的化合物可以作为未来发现和研究的模型，
• Synthesis of triterpene acids conjugates with α-tocopherol synthetic analogs
  作者：A. Yu. Spivak、R. R. Mufazzalova、E. R. Shakurova、V. N. Odinokov

  DOI：10.1134/s1070428010090150

  日期：2010.9

  Heterodimers were synthesized of pharmacologically important alpha-tocopherol synthetic analogs with triterpene acids(betulonic, betulinic), potential polyfunctionsl drugs possessing antioxidant activity. The combination of the fragments of biologically active substances was performed through linkers (residues of succinic acid, hydrazine, glycine, tetramethylenediamine) binding the side chain of the antioxidant molecule with atoms C-3 or C-28 of the terpenoid.
• Synthesis of a second generation chroman/catechol hybrids and evaluation of their activity in protecting neuronal cells from oxidative stress-induced cell death
  作者：Maria Koufaki、Elissavet Theodorou、Xanthippi Alexi、Michael N. Alexis

  DOI：10.1016/j.bmc.2010.04.042

  日期：2010.6.1

  A new generation of chroman/catechol hybrids bearing heterocyclic five-membered rings, such as 1,2, 4-oxadiazole 1,3,4-oxadiazole, 1,2,3-triazole, tetrazole and isoxazole, were designed and synthesized. The activity of the new derivatives against oxidative stress induced neuronal damage, was evaluated using glutamate-challenged hippocampal HT22 cells.Compound 3 in which a 3,4-dimethoxyphenyl moiety, is directly attached to the 1,2,4-oxadiazole ring was the most active among the 2-substituted chroman analogues, with EC50 = 254 +/- 65 nM. Concerning the 5-subtituted chroman analogues, isoxazole derivative 29 exhibited the strongest activity (EC50 = 245 +/- 38 nM). However, 29 was cytotoxic at concentrations higher than 1 mu M, while the triazole analogue 24 (EC50 = 801 +/- 229 nM), was non-toxic at all concentrations tested. (C) 2010 Elsevier Ltd. All rights reserved.