N1-(3-morpholinopropyl)benzene-1,4-diamine | 503629-23-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N1-(3-morpholinopropyl)benzene-1,4-diamine
• 英文别名: N-(3-(morpholino-4-yl)propyl)-4-aminobenzenamine；N-(3-morpholin-4-yl-propyl)-benzene-1,4-diamine；4-N-(3-morpholin-4-ylpropyl)benzene-1,4-diamine
• CAS: 503629-23-0
• 化学式: C₁₃H₂₁N₃O
• mdl: MFCD11644920
• 分子量: 235.329
• InChiKey: SSGNTACICQYKFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  50.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N1-(3-morpholinopropyl)benzene-1,4-diamine 在 对甲苯磺酸 、 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 4-((4-((3-morpholinopropyl)amino)phenyl)amino)quinoline-3-carbohydrazide
  参考文献：
  名称：

  4-Aminoquinoline derivatives as novel Mycobacterium tuberculosis GyrB inhibitors: Structural optimization, synthesis and biological evaluation

  摘要：

  Mycobacterial DNA gyrase B subunit has been identified to be one of the potentially underexploited drug targets in the field of antitubercular drug discovery. In the present study, we employed structural optimization of the reported GyrB inhibitor resulting in synthesis of a series of 46 novel quinoline derivatives. The compounds were evaluated for their in vitro Mycobacterium smegmatis GyrB inhibitory ability and Mycobacterium tuberculosis DNA supercoiling inhibitory activity. The antitubercular activity of these compounds was tested over Mtb H37Rv strain and their safety profile was checked against mouse macrophage RAW 264.7 cell line. Among all, three compounds (23, 28, and 53) emerged to be active displaying IC50 values below 1 mu M against Msm GyrB and were found to be non-cytotoxic at 50 mu M concentration. Compound 53 was identified to be potent GyrB inhibitor with 0.86 +/- 0.16 mu M and an MIC (minimum inhibitory concentration) of 3.3 mu M. The binding affinity of this compound towards GyrB protein was analysed by differential scanning fluorimetry which resulted in a positive shift of 3.3 degrees C in melting temperature (T-m) when compared to the native protein thereby reacertaining the stabilization effect of the compound over protein. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.032
• 作为产物：
  描述：

  特定基氨基甲酸脂酶 在 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 N1-(3-morpholinopropyl)benzene-1,4-diamine
  参考文献：
  名称：

  4-Aminoquinoline derivatives as novel Mycobacterium tuberculosis GyrB inhibitors: Structural optimization, synthesis and biological evaluation

  摘要：

  Mycobacterial DNA gyrase B subunit has been identified to be one of the potentially underexploited drug targets in the field of antitubercular drug discovery. In the present study, we employed structural optimization of the reported GyrB inhibitor resulting in synthesis of a series of 46 novel quinoline derivatives. The compounds were evaluated for their in vitro Mycobacterium smegmatis GyrB inhibitory ability and Mycobacterium tuberculosis DNA supercoiling inhibitory activity. The antitubercular activity of these compounds was tested over Mtb H37Rv strain and their safety profile was checked against mouse macrophage RAW 264.7 cell line. Among all, three compounds (23, 28, and 53) emerged to be active displaying IC50 values below 1 mu M against Msm GyrB and were found to be non-cytotoxic at 50 mu M concentration. Compound 53 was identified to be potent GyrB inhibitor with 0.86 +/- 0.16 mu M and an MIC (minimum inhibitory concentration) of 3.3 mu M. The binding affinity of this compound towards GyrB protein was analysed by differential scanning fluorimetry which resulted in a positive shift of 3.3 degrees C in melting temperature (T-m) when compared to the native protein thereby reacertaining the stabilization effect of the compound over protein. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.032

文献信息

• 3-(Arylamino)methylene-1, 3-dihydro-2H-indol-2-ones as kinase inhibitors
  申请人：——

  公开号：US20030199478A1

  公开（公告）日：2003-10-23

  The present invention relates to organic molecules capable of modulating tyrosine kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation.

  本发明涉及有机分子，能够调节酪氨酸激酶信号传导，以调控、调节和/或抑制异常细胞增殖。
• Design, synthesis and evaluation of 4,5-di-substituted acridone ligands with high G-quadruplex affinity and selectivity, together with low toxicity to normal cells
  作者：Francisco Cuenca、Michael J.B. Moore、Karin Johnson、Bérangère Guyen、Anne De Cian、Stephen Neidle

  DOI：10.1016/j.bmcl.2009.07.033

  日期：2009.9

  A series of 4,5-di-substituted acridones have been designed and synthesized. Several compounds show high affinity for telomeric G-quadruplex DNA in classical and competition FRET assays, together with low duplex DNA affinity, although they do not show activity in a telomerase assay or evidence of telomere shortening. They have low toxicity against a panel of cancer cell lines and a normal human fibroblast

  已经设计和合成了一系列的4，5-二取代的cri啶。几种化合物在经典和竞争性FRET分析中显示出对端粒G-四链体DNA的高亲和力，而在低端双链DNA亲和性中则低，尽管它们在端粒酶分析中没有活性，也没有端粒缩短的迹象。它们对一组癌细胞系和正常人成纤维细胞系具有低毒性，并在MCF7和A549癌细胞系中产生有效的基于衰老的长期生长停滞。
• [EN] 3-(ARYLAMINO)METHYLENE-1, 3-DIHYDRO-2H-INDOL-2-ONES AS KINASE INHIBITORS<br/>[FR] L'UTILISATION DE 3-(ARYLAMINO)METHYLENE-1, 3-DIHYDRO-2H-INDOL-2-ONES EN TANT QU'INHIBITEURS DE KINASES
  申请人：ALLERGAN INC

  公开号：WO2003027102A1

  公开（公告）日：2003-04-03

  The present invention relates to organic of general formula (I), capable of modulating tyrosine kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation.

  本发明涉及一种具有一般式(I)的有机物，能够调节酪氨酸激酶信号传导，以调节、调节和/或抑制异常细胞增殖。
• PYRIMIDINE DERIVATIVES AS PI3K INHIBITOR AND USE THEREOF
  申请人：Shimma Nobuo

  公开号：US20100069629A1

  公开（公告）日：2010-03-18

  A drug is provided that is useful as a preventive or therapeutic for cancer as a result of having superior PI3K inhibitory effects as well as superior stability in the body and water-solubility. A compound, or pharmaceutically acceptable salt thereof, represented by formula (I): [wherein, X represents a single bond, etc.; Y represents a single bond, etc. (provided that X and Y are not simultaneously single bonds); Z represents a hydrogen atom, etc.; m represents an integer of 1 or 2; and R 1 represents a cyclic substituent].

  提供了一种药物，由于具有优越的PI3K抑制作用以及在体内具有优越的稳定性和水溶性，因此可用作预防或治疗癌症。化合物或其药学上可接受的盐的表示式（I）：[其中，X表示单键等；Y表示单键等（前提是X和Y不同时为单键）；Z表示氢原子等；m表示1或2的整数；R1表示环状取代基]。
• 3-(Arylamino)methylene-1, 3-dihydro-2h-indol-2-ones as kinase inhibitors
  申请人：——

  公开号：US20030225152A1

  公开（公告）日：2003-12-04

  The present invention relates to organic molecules capable of modulating tyrosine kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation.

  本发明涉及有机分子，能够调节酪氨酸激酶信号传导，以调节、调制和/或抑制异常细胞增殖。