4-ethoxy-5-methoxy-2-nitrobenzonitrile | 861306-97-0

• 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: 4-ethoxy-5-methoxy-2-nitrobenzonitrile
• CAS: 861306-97-0
• 化学式: C₁₀H₁₀N₂O₄
• 分子量: 222.2
• InChiKey: CPCWUWQVAMBARW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  85.39
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-ethoxy-5-methoxy-2-nitrobenzonitrile 在 盐酸 、 palladium 10% on activated carbon 、 环己烯 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of substituted 1,2,3-benzotriazines and pyrido[3,2-d]-1,2,3-triazines as inhibitors of vascular endothelial growth factor receptor-2

  摘要：

  A novel series of substituted 1,2,3-benzotriazines and pyrido[3,2-d]-1,2,3-triazines were synthesized. The abilities of these compounds to inhibit the VEGFR-2 kinase activity and the proliferation of human microvascular endothelial cells (MVECs) were determined. 6-Methoxy-4-substituted-1,2,3-benzotriazines and 4-substituted-6-chloro-pyrido[3,2-d]-1,2,3-triazines have the abilities of inhibiting the VEGFR-2 kinase activity, but only the 4-substituted-6-chloro-pyrido[3,2-d]-1,2,3-triazines exhibit good growth inhibitory effects on MVECs. Compound 6-chloro-4-(3-trifluoromethylanilino)-pyrido[3,2-d][1,2,3] triazin (11d) is less half active than PTK787 to inhibit the VEGFR-2 kinase activity, but is more active than PTK787 to inhibit the growth of MVECs. The potential binding modes of 6d, 11d, and CTZ12 in complex with their putative intracellular target, VEGFR-2, were predicted using Surflex-Dock. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.009
• 作为产物：
  描述：

  4-羟基-3-甲氧基苯甲腈 在 硝酸 、 乙酸酐 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.58h， 生成 4-ethoxy-5-methoxy-2-nitrobenzonitrile
  参考文献：
  名称：

  Structure–activity relationship studies of SETD8 inhibitors

  摘要：

  对第一个底物竞争性SETD8抑制剂的全面SAR研究揭示了有趣的SAR趋势和新颖的类似物。

  DOI：

  10.1039/c4md00317a

文献信息

• Discovery of Potent and Selective Inhibitors for G9a-Like Protein (GLP) Lysine Methyltransferase
  作者：Yan Xiong、Fengling Li、Nicolas Babault、Aiping Dong、Hong Zeng、Hong Wu、Xin Chen、Cheryl H. Arrowsmith、Peter J. Brown、Jing Liu、Masoud Vedadi、Jian Jin

  DOI：10.1021/acs.jmedchem.6b01645

  日期：2017.3.9

  and G9a are highly homologous protein lysine methyltransferases (PKMTs) sharing approximately 80% sequence identity in their catalytic domains. GLP and G9a form a heterodimer complex and catalyze mono- and dimethylation of histone H3 lysine 9 and nonhistone substrates. Although they are closely related, GLP and G9a possess distinct physiological and pathophysiological functions. Thus, GLP or G9a selective

  G9a样蛋白（GLP）和G9a是高度同源的蛋白赖氨酸甲基转移酶（PKMT），在其催化域中共有大约80％的序列同一性。GLP和G9a形成异二聚体复合物，并催化组蛋白H3赖氨酸9和非组蛋白底物的单和二甲基化。尽管它们密切相关，但GLP和G9a具有独特的生理和病理生理功能。因此，GLP或G9a选择性小分子抑制剂是剖析其独特生物学功能的有用工具。我们以前曾报道过强效和选择性的G9a / GLP双重抑制剂，包括UNC0638和UNC0642。在这里，我们报告发现了有效和选择性的GLP抑制剂，包括4种（MS0124）和18种（MS012），其对GLP的选择性分别是G9a和其他甲基转移酶的30倍和140倍。具有4或18个复合物的GLP和G9a的共晶体结构显示出几乎相同的结合模式和相互作用，这突出显示了针对两种酶的选择性抑制剂的基于结构设计的挑战。
• Design, Synthesis, and Antitumor Activities of Some Novel Substituted 1,2,3-Benzotriazines
  作者：Jin-Ling Lv、Rui Wang、Dan Liu、Gang Guo、Yong-Kui Jing、Lin-Xiang Zhao

  DOI：10.3390/molecules13061427

  日期：——

  A series of novel substituted 1,2,3-benzotriazines based on the structures of vatalanib succinate (PTK787) and vandetanib (ZD6474) were designed and synthesized. The antiproliferative effects of these compounds were tested on microvascular endothelial cells (MVECs) using the MTT assay. Introduction of a methoxy and a 3-chloropropoxy group into the 1,2,3-benzotriazines increased the antiproliferative effects. 4-(3-Chloro-4- fluoroanilino)-7-(3-chloropropoxy)-6-methoxy-1,2,3-benzotriazine (8m) was the most effective compound. It was 4-10 fold more potent than PTK787 in inhibiting the growth of T47D breast cancer cells, DU145 and PC-3 prostate cancer cells, LL/2 murine Lewis lung cancer cells and B16F0 melanoma cells.

  基于舒尼替（PTK787）和凡德他尼（ZD6474）的结构，设计并合成了一系列新型取代的1,2,3-苯并三嗪。通过MTT assay测试了这些化合物对微血管内皮细胞（MVECs）的抗增殖作用。在1,2,3-苯并三嗪中引入甲氧基和3-氯丙氧基增强了抗增殖效应。4-(3-氯-4-氟苯胺)-7-(3-氯丙氧基)-6-甲氧基-1,2,3-苯并三嗪（8m）是最有效的化合物。它对T47D乳腺癌细胞、DU145和PC-3前列腺癌细胞、LL/2小鼠路易斯肺癌细胞和B16F0黑色素瘤细胞的抑制生长作用比PTK787强4-10倍。
• Keffler, Journal of the Chemical Society, 1921, vol. 119, p. 1478
  作者：Keffler

  DOI：——

  日期：——