1-(2-氨基-5-甲基苯基)-2-氯乙酮 | 61871-80-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-氨基-5-甲基苯基)-2-氯乙酮
• 英文名称: 2-Amino-α-chlor-5-methylacetophenon
• 英文别名: 1-(2-amino-5-methyl-phenyl)-2-chloro-ethanone；1-(2-Amino-5-methyl-phenyl)-2-chlor-aethanon；ω-Chlor-6-amino-3-methyl-acetophenon；4-Amino-3-chloracetyl-toluol；5-methyl-2-amino-α-chloroacetophenone；1-(2-Amino-5-methylphenyl)-2-chloroethan-1-one；1-(2-amino-5-methylphenyl)-2-chloroethanone
• CAS: 61871-80-5
• 化学式: C₉H₁₀ClNO
• 分子量: 183.637
• InChiKey: HYBQWJSRAVOXSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-氨基-5-甲基苯基)-2-氯乙酮 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以81%的产率得到5-甲基吲哚
  参考文献：
  名称：

  Nimtz, Manfred; Haefelinger, Guenter, Liebigs Annalen der Chemie, 1987, p. 765 - 770

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(Acetylamino)-α-chlor-5-methylacetophenon 在 盐酸 作用下， 生成 1-(2-氨基-5-甲基苯基)-2-氯乙酮
  参考文献：
  名称：

  Kunckell, Chemische Berichte, 1900, vol. 33, p. 2647,2649

  摘要：

  DOI：

文献信息

• Synergistic Cooperative Effect of Sodium borohydride-Iodine Towards Cascade C−N and C−S/Se Bond Formation: One-pot Regioselective Synthesis of 3-Sulfenyl/selenyl Indoles and Mechanistic Insight
  作者：Aditya G. Lavekar、Danish Equbal、Saima、Arun K. Sinha

  DOI：10.1002/adsc.201701028

  日期：2018.1.4

  into synergistic cooperative effect of NaBH4‐I2 which allows cascade C−N and C−S/C−Se bond formations via reduction‐nucleophilic cyclization‐chalcogenylation, three steps in one‐pot, towards regioselective synthesis of diverse 3‐chalcogenyl indoles including 5‐bromo‐3‐[(3,4,5‐trimethoxyphenyl)thio]‐1H‐indole, a known lead anticancer compound, directly from 2‐amino‐phenacylchlorides and thiophenols or

  在这项工作中，报道了一种合成3-亚磺酰基/硒基吲哚的新策略，其中LC-MS揭示了对NaBH 4 -I 2的协同协同作用的新颖见解，该协同作用允许级联CN和CS / C-Se键通过还原-亲核环化-硫代烷基化反应形成三步反应，形成区域选择性合成各种3-硫代半胱氨酸吲哚，包括5-溴-3-[（3,4,5-三甲氧基苯基）硫代] -1H-吲哚已知的先导抗癌化合物，直接来自2-氨基-苯甲酰氯和硫酚或二硫化物/二硒化物在无过渡金属条件下的二恶烷水溶液中。
• Indole‐based aryl sulfides target the cell wall of <i>Staphylococcus aureus</i> without detectable resistance
  作者：Aditya G. Lavekar、Ritesh Thakare、Saima、Danish Equbal、Sidharth Chopra、Arun K. Sinha

  DOI：10.1002/ddr.22123

  日期：2024.2

  Sulfur‐containing classes of the scaffold “Arylthioindoles” have been evaluated for antibacterial activity; they demonstrated excellent potency against methicillin‐resistant Staphylococcus aureus (MRSA) as well as against vancomycin‐resistant strains and a panel of clinical isolates of resistant strains. In this study, we have elucidated the mechanism of action of lead compounds, wherein they target the cell wall of S. aureus. Further, S. aureus failed to develop resistance against two lead compounds tested in a serial passage experiment in the presence of the compounds over a period of 40 days. Both the compounds demonstrated comparable in vivo efficacy with vancomycin in a neutropenic mice thigh infection model. The results of these antibacterial activities emphasize the excellent potential of thioethers for developing novel antibiotics and may fill in as a target for the adjustment of accessible molecules to develop new powerful antibacterial agents with fewer side effects.

  摘要 已经对 "芳硫基吲哚 "支架的含硫类化合物进行了抗菌活性评估；这些化合物对耐甲氧西林金黄色葡萄球菌（MRSA）、耐万古霉素菌株和耐药菌株的临床分离物均表现出卓越的效力。在这项研究中，我们阐明了先导化合物的作用机制，即它们靶向金黄色葡萄球菌的细胞壁。此外，在对两种先导化合物进行了为期 40 天的连续培养实验后，金黄色葡萄球菌未能对这两种先导化合物产生耐药性。在嗜中性粒细胞小鼠大腿感染模型中，这两种化合物的体内疗效与万古霉素相当。这些抗菌活性的结果突出了硫醚在开发新型抗生素方面的巨大潜力，并可能成为调整可获得分子的目标，从而开发出副作用更小的新型强效抗菌剂。
• Substituted kynurenines, a process for their preparation, and use as medicaments
  申请人：THE UNIVERSITY OF MARYLAND AT BALTIMORE

  公开号：EP0919538A1

  公开（公告）日：1999-06-02

  The present invention relates to the use in the treatment of cognitive disorders associted with the aging processes of the brain and perinatal brain disorders of compounds which act as inhibitors of the enzyme kynurenine aminotransferase (KAT). The present invention also provides, as novel compounds, a selected class of KAT inhibitors which are the compounds of formula (IA), wherein R is halogen, C1-C6 alkyl, C5-C7 cycloalkyl, phenyl-C1-C4 alkyl, C1-C6 alkoxy, C6-C10 aryloxy, phenyl-C1-C4 alkoxy or trifluoromethyl, and R1 is hydroxy, C1-C6 alkoxy, amino, mono-C1-C6 alkylamino di-C1-C6 alkylamino, hydroxylamino, C1-C4 alkoxyamino or benzyloxyamino, with the provisos that: (i) when R1 is hydroxy and at the same time, R is halogen, then this halogen is not fluorine; and (ii) when R1 is hydroxy and, at the same time, R is C1-C6 alkyl, then this C1-C6 alkyl is not methyl, either as a single isomer or as a mixture of isomers, and the pharmaceutically acceptable salts thereof.

  本发明涉及作为犬尿氨酸氨基转移酶（KAT）抑制剂的化合物在治疗与大脑衰老过程有关的认知障碍和围产期大脑障碍中的应用。C6-C10芳氧基、苯基-C1-C4 烷氧基或三氟甲基，而 R1 是羟基、C1-C6 烷氧基、氨基、单-C1-C6 烷基氨基、二-C1-C6 烷基氨基、羟基氨基、C1-C4 烷氧基氨基或苄氧基氨基，但前提是(i) 当 R1 是羟基，同时 R 是卤素时，该卤素不是氟；以及 (ii) 当 R1 是羟基，同时 R 是 C1-C6 烷基时，该 C1-C6 烷基不是甲基，可以是单一异构体，也可以是异构体的混合物，以及它们的药学上可接受的盐。
• Synthesis and bioevaluation of 22-hydroxyacuminatine analogs
  作者：François Grillet、Barbora Baumlová、Grégoire Prévost、Jean-François Constant、Sophie Chaumeron、Dennis C.H. Bigg、Andrew E. Greene、Alice Kanazawa

  DOI：10.1016/j.bmcl.2008.01.082

  日期：2008.3

  A series of 22-hydroxyacuminatine analogs was prepared by using different Friedlander condensations. Several of the new compounds were tested for antiproliferative activity on cancer cell lines and for topoisomerase I inhibitory activity. (c) 2008 Elsevier Ltd. All rights reserved.
• New homocamptothecins: Synthesis, antitumor activity, and molecular modeling
  作者：Zhenyuan Miao、Chunquan Sheng、Wannian Zhang、Haitao Ji、Jing Zhang、Lücheng Shao、Liang You、Min Zhang、Jianzhong Yao、Xiaoyin Che

  DOI：10.1016/j.bmc.2007.10.046

  日期：2008.2.1

  Homocamptothecins (hCPTs) represent a class of new emerging antitumor agents, which contains a seven-membered beta-hydroxylactone in place of the conventional six-membered alpha-hydroxylactone ring (E ring) of camptothecins. Some novel 7-substituted hCPTs were designed and synthesized based on a newly developed synthetic route which couples ring A with ring C, E and D. Most of the synthesized compounds exhibit very high cytotoxic activity on tumor cell line A549. Some compounds, such as 9b, 91, and 9y, show broad in vitro antitumor spectrum and are more potent than topotecan. Three-dimensional quantitative structure-activity relationship (3D-QSAR) methods, CoMFA and CoMSIA, were applied to explain the structure-activity relationship (SAR) of the synthesized compounds. Furthermore, molecular docking was used to clarify the binding mode of the synthesized compounds to human DNA topoisomerase I. The important hydrophobic, base-pair stacking, and hydrogen-bonding interactions were observed between the hCPT derivatives and their receptor. The results from molecular modeling will guide the design of novel hCPTs with higher antitumor activity. (C) 2007 Elsevier Ltd. All rights reserved.