[(4-三氟甲基苯基)肼基]氯乙酸乙酯 | 1202942-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [(4-三氟甲基苯基)肼基]氯乙酸乙酯
• 英文名称: ethyl 2-chloro-2-[[4-(trifluoromethyl)phenyl]hydrazono]acetate
• 英文别名: ethyl 2-chloro{[4-(trifluoromethyl)phenyl]-hydrazono}ethanoate；[(4-trifluoromethylphenyl)-hydrazono]-chloroacetic acid ethyl ester；Ethyl 2-chloro-2-[[4-(trifluoromethyl)phenyl]hydrazinylidene]acetate；ethyl 2-chloro-2-[[4-(trifluoromethyl)phenyl]hydrazinylidene]acetate
• CAS: 1202942-25-3
• 化学式: C₁₁H₁₀ClF₃N₂O₂
• 分子量: 294.661
• InChiKey: FYRZZKRMSIAUPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(4-三氟甲基苯基)肼基]氯乙酸乙酯 在 lithium aluminium tetrahydride 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 、 甲苯 为溶剂， 反应 4.5h， 生成 3-(chloromethyl)-4-methyl-1-[4-(trifluoromethyl)phenyl]pyrazole
  参考文献：
  名称：

  [EN] NOVEL PIPERIDINE DERIVATIVES
  [FR] NOUVEAUX DÉRIVÉS DE PIPÉRIDINE

  摘要：

  这项发明涉及一种化合物，其化学式为（I），其中A1，A2和R1至R3的定义如描述和索赔中所述。化合物的化学式（I）可用作药物。

  公开号：

  WO2016087352A1
• 作为产物：
  描述：

  p-(trifluoromethyl)benzenediazonium tetrafluoroborate 、 2-氯乙酰乙酸乙酯 以 吡啶 、 水 为溶剂， 反应 0.5h， 以90%的产率得到[(4-三氟甲基苯基)肼基]氯乙酸乙酯
  参考文献：
  名称：

  Synthesis and Structure−activity Relationships of Antitubercular 2-Nitroimidazooxazines Bearing Heterocyclic Side Chains

  摘要：

  Recently described biphenyl analogues Of the antituberculosis drug PA-824 displayed improved potencies against M. tuberculosis but were poorly soluble. Heterobiaryl analogues of these, in which the first phenyl ring was replaced with various 5-membered ring heterocycles, were prepared with the aim of identifying potent new candidates with improved aqueous solubility. The compounds were constructed by coupling the chiral 2-nitroimidazooxazine alcohol with various halomethyl-substituted arylheterocycles, by cycloadditions to a propargyl ether derivative of this alcohol, or by Suzuki couplings on haloheterocyclic methyl ether derivatives. The arylheterocyclic compounds were all more hydrophilic than their corresponding biphenyl analogues, and several showed solubility improvements. 1-Methylpyrazole, 1,3-linked-pyrazole, 2,4-linked-triazole, and tetrazole analogues had 3- to 7-fold higher MIC potencies against replicating M. tb than predicted by their lipophilicities. Two pyrazole analogues were >10-fold more efficacious than the parent drug in a mouse model of acute M. tb infection, and one displayed a 2-fold higher solubility.

  DOI：

  10.1021/jm901378u

文献信息

• One-flask synthesis of 1,3,5-trisubstituted 1,2,4-triazoles from nitriles and hydrazonoyl chlorides via 1,3-dipolar cycloaddition
  作者：Li-Ya Wang、Henry J. Tsai、Hui-Yi Lin、Kimiyoshi Kaneko、Fen-Ying Cheng、Hsin-Siao Shih、Fung Fuh Wong、Jiann-Jyh Huang

  DOI：10.1039/c4ra00113c

  日期：——

  One-flask synthesis of 1,3,5-trisubstituted 1,2,4-triazoles from nitriles and hydrazonoyl chlorides via 1,3-dipolar cycloaddition.

  一瓶法合成1,3,5-三取代-1,2,4-三唑，从腈和叠氮酰氯通过1,3-偶极环加成。
• Synthesis of novel pyrazoles incorporating a phenothiazine moiety: unambiguous structural characterization of the regioselectivity in the 1,3-dipolar cycloaddition reaction using 2D HMBC NMR spectroscopy
  作者：Ahmed E.M. Mekky、Tamer S. Saleh、Abdullah S. Al-Bogami

  DOI：10.1016/j.tet.2013.06.028

  日期：2013.8

  An efficient and attractive regioselective synthesis of a series of novel pyrazoles containing a phenothiazine moiety was achieved utilizing microwave irradiation. Unambiguous structural assignment of the obtained regioisomers was determined utilizing 2D HMBC NMR techniques as a valuable tool.

  利用微波辐照实现了一系列新颖的含有吩噻嗪部分的吡唑的高效和有吸引力的区域选择性合成。 使用2D HMBC NMR技术作为有价值的工具，确定了所获得的区域异构体的明确结构分配。
• Design, synthesis and anti-tumor evaluation of 1,2,4-triazol-3-one derivatives and pyridazinone derivatives as novel CXCR2 antagonists
  作者：Xun Zhang、Jingyi Luo、Qinyuan Li、Qilei Xin、Lizhen Ye、Qingyun Zhu、Zhichao Shi、Feng Zhan、Bizhu Chu、Zijian Liu、Yuyang Jiang

  DOI：10.1016/j.ejmech.2021.113812

  日期：2021.12

  therapy. CXCR2 antagonists could block CXCLs/CXCR2 axis, and are widely used in regulating immune cell migration, tumor metastasis, apoptosis and angiogenesis. Herein, two series of new CXCR2 small-molecule inhibitors, including 1,2,4-triazol-3-one derivatives 1–11 and pyridazinone derivatives 12–22 were designed and synthesized based on the proof-to-concept. The pyridazinone derivative 18 exhibited

  趋化因子受体 2 (CXCR2) 是含有谷氨酸-亮氨酸-精氨酸序列的趋化因子 CXCs (ELR + CXCs) 的受体。近年来，CXCR2靶向治疗策略在癌症治疗中取得了长足的进步。CXCR2拮抗剂可阻断CXCLs/CXCR2轴，广泛用于调节免疫细胞迁移、肿瘤转移、细胞凋亡和血管生成。在此，基于概念验证设计和合成了两个系列的新型CXCR2小分子抑制剂，包括 1,2,4-triazol-3-one 衍生物1-11和哒嗪酮衍生物12-22 。哒嗪酮衍生物18表现出良好的 CXCR2 拮抗活性（10 μM 时为 69.4 ± 10.5 %Inh），并在 MDA-MB-231 细胞中表现出显着的抗癌转移活性，在 HUVEC 中表现出显着的抗血管生成活性。此外，值得注意的是，18在MDA-MB-231细胞的抗增殖试验中与索拉非尼表现出明显的协同作用。此外，18显示 MDA-MB-231 细胞中 PI3K
• Microwave-assisted Regioselective Synthesis of Novel Bis(azoles) and Bis(azoloazines)
  作者：Abdullah S. Al-Bogami、Ahmed E. M. Mekky

  DOI：10.1002/jhet.2462

  日期：2016.9

  We introduce efficient regioselective synthesis of a series of novel bis(pyrazoles) and bis(isoxazoles) via 1,3‐dipolar cycloaddition reaction under microwave irradiation. Unequivocal structural assignment of the obtained regioisomers was determined utilizing 1H‐13C HMBC NMR techniques as a valuable tool. A comparative study of the aforementioned reactions was carried out under conventional method

  通过微波辐射下的1,3-偶极环加成反应，我们介绍了有效的区域选择性合成一系列新型双（吡唑）和双（异恶唑）的方法。使用1 H- 13 C HMBC NMR技术作为有价值的工具确定了获得的区域异构体的明确结构分配。在常规方法以及微波辐射条件下进行了上述反应的比较研究。
• Design, synthesis, and photophysics of bi- and tricyclic fused pyrazolines
  作者：Alexandra V. Popova、Ali Kanaa、Vladislava S. Vavilova、Maria A. Mironova、Pavel A. Slepukhin、Enrico Benassi、Nataliya P. Belskaya

  DOI：10.1039/d0nj06287a

  日期：——

  Three series of bi- and tricyclic functionalized new pyrazoline fluorophores have been synthesized for investigation of their photophysical properties. Spectral studies indicated significant absorption and emission properties. The quantum yields reached 93% and Stokes shifts increased up to 148 nm. The compounds exhibited positive solvato(fluoro)chromism. Fluorescence was sensitive to both structural

  合成了三个系列的双环和三环功能化的新型吡唑啉荧光团，以研究其光物理性质。光谱研究表明明显的吸收和发射性质。量子产率达到93％，斯托克斯位移增加到148 nm。该化合物表现出正溶剂化（氟）色度。荧光对结构变化和微环境都敏感，特别是对质子溶剂，如EtOH，n -BuOH和DMSO / H 2敏感O的混合物，与乙二醇。实验结果得到了量子力学计算的支持。取代基的电子性质及其空间效应的修饰可以改变分子内电荷转移（ICT）的性质和方向。这些发现为开发具有可调光物理性质的新型稠合吡唑啉提供了宝贵的见识。吡唑啉表现出高强度的固态发射，使其适合用于光子学。活性官能团可用于结合吡唑啉和天然化合物，药物和诊断分子，以用于生物系统和药物中。