2-氨基-4-甲氧基-3-(3-吗啉丙氧基)苯甲酸甲酯 | 214472-41-0

• 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: 2-氨基-4-甲氧基-3-(3-吗啉丙氧基)苯甲酸甲酯
• 英文名称: methyl 2-amino-4-methoxy-5-(3-morpholinopropoxy)benzoate
• 英文别名: methyl 2-amino-4-methoxy-5-(3-morpholin-4-ylpropoxy)benzoate
• CAS: 214472-41-0
• 化学式: C₁₆H₂₄N₂O₅
• 分子量: 324.377
• InChiKey: DFJJAQKKQNIWOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  83.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-氨基-4-甲氧基-3-(3-吗啉丙氧基)苯甲酸甲酯 在 N,N-二甲基甲酰胺 正丁基锂 、 氯化亚砜 、 吡啶盐酸盐 作用下， 以 四氢呋喃 、 乙二醇乙醚 、 正己烷 为溶剂， 反应 7.75h， 生成 4-(4-chloro-2-fluoro-5-hydroxy-phenylamino)-7-methoxy-6-(3-morpholin-4-yl)-propoxyl-quinoline-3-carbonitrile
  参考文献：
  名称：

  SUBSTITUTED 3-CYANO QUINOLINES

  摘要：

  公开号：

  EP0973746B1
• 作为产物：
  描述：

  4-甲氧基-3-(3-(吗啉-4-基)丙氧基)苯甲酸甲酯 在 palladium on activated charcoal 氢气 、 硝酸 、 溶剂黄146 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 2-氨基-4-甲氧基-3-(3-吗啉丙氧基)苯甲酸甲酯
  参考文献：
  名称：

  Syntheses and EGFR and HER-2 kinase inhibitory activities of 4-anilinoquinoline-3-carbonitriles: analogues of three important 4-anilinoquinazolines currently undergoing clinical evaluation as therapeutic antitumor agents

  摘要：

  The syntheses and biological evaluations of 4-anilinoquinoline-3-carbonitrile analogues of the three clinical lead 4-anilinoquinazolines Iressa(TM), Tarceva(TM), and CI-1033 are described. The EGFR and HER-2 kinase inhibitory activities and the cell growth inhibition of the two series are compared with each other and with the clinical lead EKB-569. Similar activities are observed between these two series. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00598-x

文献信息

• Method of Synthesizing 6,7-Substituted 4-Anilino Quinazoline
  申请人：Shih Kae-Shyang

  公开号：US20100267949A1

  公开（公告）日：2010-10-21

  A method of synthesizing 6,7-substituted 4-anilino quinazoline employs 3,4-substituted benzoic acid as an initial reactant, and the 6,7-substituted 4-anilino quinazoline is obtained by an esterifying step, a nitrating step, a reducing step, a cyclizing step, and an one-pot reaction. In the above method, the initial reactant has low cost and yield. of the 6,7-substituted 4-anilino quinazoline is high, therefore, production cost can be reduced effectively, and competitive power of the product of the 6,7-substituted 4-anilino quinazoline can be improved.

  合成6,7-取代的4-苯胺喹唑啉的方法采用3,4-取代苯甲酸作为初始反应物，通过酯化步骤、硝化步骤、还原步骤、环化步骤和一锅法反应得到6,7-取代的4-苯胺喹唑啉。在上述方法中，初始反应物成本低且产率高。6,7-取代的4-苯胺喹唑啉的产率高，因此可以有效降低生产成本，提高6,7-取代的4-苯胺喹唑啉产品的竞争力。
• SUBSTITUTED 4-(SELENOPHEN-2(OR-3)-YLAMINO)PYRIMIDINE COMPOUNDS AND METHODS OF USE THEREOF
  申请人：KASINA LAILA INNOVA PHARMACEUTICALS PRIVATE LIMITED

  公开号：US20130266563A1

  公开（公告）日：2013-10-10

  Selenophene compounds of formula (I) are described herein. In the compounds of Formula (I), ring A is a 6-membered aromatic fused ring, optionally containing one, two or three nitrogen atoms; a 5-membered heteroaromatic fused ring; or a mono- or bicyclic saturated heterocyclic fused ring having at least one ring member selected from the group consisting of N, O, S, SO and SO 2 ; Y in ring B is nitrogen or substituted carbon; X is NR 6 , O, S, S(O), or S(O) 2 . R 1 , R 2 , R 3 , R 4 , and R 6 are defined in the specification. Selenophene compounds of formula (I) may be used in methods of treating cell proliferative disorders, particularly cancer. Pharmaceutical compositions containing selenophene compounds of formula (I) may be used for treatment, inhibition, or control of cancer.

  Selenophene化合物的化学式（I）在此描述。在化合物的化学式（I）中，环A是一个6元芳香融合环，可选地含有一个、两个或三个氮原子；一个5元杂芳融合环；或者至少有一个环成员选自N、O、S、SO和SO2的单环或双环饱和杂环融合环；环B中的Y是氮或取代碳；X是NR6、O、S、S（O）或S（O）2。R1、R2、R3、R4和R6在规范中有定义。化学式（I）的Selenophene化合物可用于治疗细胞增殖紊乱的方法，特别是癌症。含有化学式（I）的Selenophene化合物的药物组合物可用于治疗、抑制或控制癌症。
• Fluorine-18 labeling of 6,7-disubstituted anilinoquinazoline derivatives for positron emission tomography (PET) imaging of tyrosine kinase receptors: synthesis of18F-Iressa and related molecular probes
  作者：Yann Seimbille、Michael E. Phelps、Johannes Czernin、Daniel H. S. Silverman

  DOI：10.1002/jlcr.998

  日期：2005.10.15

  radiolabeled 6,7-disubstituted 4-anilinoquinazolines suitable for noninvasive imaging of tyrosine kinase receptors to predict therapy effectiveness. Three new F-18 labeled radiopharmaceuticals based on the therapeutic agents Tarceva, Iressa, and ZD6474 were synthesized. Decay-corrected yields varied between 25 and 40% for a total synthesis time of 120 min, thus providing F-18 labeled tyrosine kinase inhibitors

  酪氨酸激酶酶活性抑制剂代表了一类有前途的抗肿瘤药物。尽管在过去十年中进行的临床研究对此类药物的潜在治疗应用提供了更多见解，但识别可能从中受益的个体患者仍然是一个重大挑战。我们开发了一种合成策略，用于生产各种放射性标记的 6,7-二取代 4-苯胺喹唑啉，适用于酪氨酸激酶受体的无创成像，以预测治疗效果。合成了三种基于治疗剂特罗凯、易瑞沙和 ZD6474 的新型 F-18 标记放射性药物。对于 120 分钟的总合成时间，衰减校正的产率在 25% 和 40% 之间变化，从而提供 F-18 标记的酪氨酸激酶抑制剂，其数量和时间可用作 PET 放射性药物。版权所有 © 2005 John Wiley & Sons, Ltd.
• Novel Preparation of gefitinib
  作者：Youguang Zheng、Mingdong Li、Shaoning Zhang、Min Ji

  DOI：10.3184/030823409x460740

  日期：2009.6

  A new synthesis of the anticancer drug gefitinib is described starting from methyl 3-hydroxy-4-methoxybenzoate. The sequence involves alkylation of the starting material, followed by nitration, reduction, cyclisation, chlorination and amination reactions. This new method has six steps, uses a much cheaper starting material and has higher yields than other methods. It is suitable for industrial production.

  本文介绍了一种以 3-羟基-4-甲氧基苯甲酸甲酯为起始原料合成抗癌药物吉非替尼的新方法。合成顺序包括起始原料的烷基化，然后是硝化、还原、环化、氯化和胺化反应。与其他方法相比，这种新方法有六个步骤，使用的起始原料便宜得多，产量也更高。它适用于工业生产。
• RETRACTED: A new heterocyclic compound initiates ROS accumulation and cause apoptotic cell death in human bone cancer cells
  作者：Guang Lv、Chong-Lan Yin

  DOI：10.1016/j.molstruc.2019.03.035

  日期：2019.6

  results revealed that compound 1 could block the proliferation of Saos-2 bone cancer cells. In addition, Annexin V-FITC/PI assay and Western blot analysis were performed to detect whether compound 1 could induce cell apoptosis. The results indicated that compound 1 could increase the number of apoptotic cells remarkably. Moreover, we examined the impact of compound 1 on ROS generation. Results revealed

  摘要 以5-羟基-4-甲氧基-2-硝基苯甲酸甲酯(2)为原料设计的新型杂环化合物7-甲氧基-6-(3-吗啉代丙氧基)喹唑啉-4(3H)-一(1)，通过多种合成途径成功获得，最终通过傅里叶变换红外（FT-IR）光谱、1H核磁共振（NMR）和单晶X射线晶体学表征。我们使用 Cell Counting Kit-8 (CCK8) 测定研究了其对细胞活力和增殖的影响。结果表明，化合物1可以阻断Saos-2骨癌细胞的增殖。此外，还进行了Annexin V-FITC/PI检测和Western Blot分析以检测化合物1是否能诱导细胞凋亡。结果表明，化合物1可显着增加凋亡细胞的数量。而且，我们检查了化合物 1 对 ROS 生成的影响。结果表明，化合物 1 上调活性氧 (ROS) 基因表达并促进 ROS 在 Saos-2 细胞中的积累。最后，分子对接已被用于研究化合物 1 与微管蛋白的结合模式。