2-(m-Nitro-benzylidenamino)-p-kresol | 19430-27-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(m-Nitro-benzylidenamino)-p-kresol
• 英文别名: 4-Methyl-2-[(3-nitrophenyl)methylideneamino]phenol
• CAS: 19430-27-4
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: FRQUURKOTBHIBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(m-Nitro-benzylidenamino)-p-kresol 在 sodium tetrahydroborate 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 17.0h， 生成 N-(3-nitrobenzyl)-5-methylbenzoxazol-2-thione
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of New N-(Phenylmethyl)-benzoxazol-2-thiones as Macrophage Migration Inhibitory Factor (MIF) Antagonists: Efficacies in Experimental Pulmonary Hypertension

  摘要：

  Macrophage migration inhibitory factor (MIF) is a key pleiotropic mediator and a promising therapeutic target in cancer as well as in several inflammatory and cardiovascular diseases including pulmonary arterial hypertension (PAH). Here, a novel series of N-(phenylmethyl)-benzoxazol-2-thiones 5-32 designed to target the MIF tautomerase active site was synthesized and evaluated for its effects on cell survival. Investigation of structure-activity relationship (SAR) particularly at the 5-position of the benzoxazole core led to the identification of 31 that potently inhibits cell survival in DU-145 prostate cancer cells and pulmonary endothelial cells derived from patients with idiopathic PAH (iPAH-ECs), two cell lines for which survival is MIF-dependent. Molecular docking studies helped to interpret initial SAR related to MIF tautomerase inhibition and propose preferred binding mode for 31 within the MIF tautomerase active site. Interestingly, daily treatment with 31 started 2 weeks after a subcutaneous monocrotaline injection regressed established pulmonary hypertension in rats.

  DOI：

  10.1021/acs.jmedchem.7b01312
• 作为产物：
  描述：

  间硝基苯甲醛 、 邻氨基对甲苯酚 以 甲醇 为溶剂， 反应 24.0h， 生成 2-(m-Nitro-benzylidenamino)-p-kresol
  参考文献：
  名称：

  A new and efficient one-pot synthesis of 2-hydroxy-1,4-dihydrobenzoxazines via a three-component Petasis reaction

  摘要：

  DOI：

  10.1016/j.tetlet.2014.07.093

文献信息

• Ruthenium(III) Cyclometalates Obtained by Site‐Specific Orthometallation and Their Reactivity with Nitric Oxide: Photoinduced Release and Estimation of NO Liberated from the Ruthenium Nitrosyl Complexes
  作者：Kaushik Ghosh、Sushil Kumar、Rajan Kumar、Udai P. Singh

  DOI：10.1002/ejic.201101026

  日期：2012.2

  spectra. Molecular structures of σ-aryl ruthenium nitrosyl complexes 1a·CH3OH·2CH2Cl2·H2O and 2a·2CH2Cl2 were determined by X-ray crystallography. Nitrosylation at the metal centre, oxidative cyclization and ligand nitration were authenticated from the crystal structures. The redox properties of the metal centre were investigated. In both the nitrosyl complexes 1a and 2a, coordinated NO was found to

  环金属化 RuIII 配合物 [Ru(LSB1)(PPh3)2Cl] (1), [LSB1H2 = 2-(3-nitrobenzylideneamino)phenol] 和 [Ru(LSB2)(PPh3)2Cl] (2), [LSB2H2 = 4-甲基-2-（3-硝基亚苄基氨基）苯酚和 H = 可解离质子]，通过位点特异性正金属化合成，并通过光谱和电化学研究进行表征。配合物 1 和 2 用原位生成的一氧化氮 (NO) 处理，该氧化氮源自酸化的亚硝酸盐溶液，得到亚硝酰基钌配合物 [Ru(LSB3H)(PPh3)2(NO)Cl](ClO4) (1a) 和[Ru(LBOX)(PPh3)2(NO)Cl]( ) (2a), [LSB3H2 = 4-nitro-2-(3-nitrobenzlideneamino)phenol, LBOXH = 5-methyl-7-nitro-2 -(3-硝基苯基)苯并恶唑和