4-chloro-3-methyl-5-nitroquinoline | 134992-33-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-chloro-3-methyl-5-nitroquinoline
• 英文别名: 4-Chlor-3-methyl-5-nitro-chinolin
• CAS: 134992-33-9
• 化学式: C₁₀H₇ClN₂O₂
• 分子量: 222.631
• InChiKey: CDWKPDLJNIANPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-3-methyl-5-nitroquinoline 在 钯 作用下， 以to give 3-methyl-5-aminoquinoline的产率得到3-methylquinolin-5-amine
  参考文献：
  名称：

  N-aryl and N-heteroarylamide and urea derivatives as inhibitors of acyl

  摘要：

  式子为##STR1##的化合物及其药学上可接受的盐，其中Q和R.sup.1的定义如下，以及在合成这种化合物时使用的新型羧酸和酸卤代中间体。式I的化合物是酰基辅酶A：胆固醇酰基转移酶（ACAT）的抑制剂，可用作降脂和抗动脉粥样硬化剂。

  公开号：

  US05656634A1
• 作为产物：
  描述：

  3-甲基-4-氯喹啉 在 硫酸 、 硝酸 作用下， 生成 4-chloro-3-methyl-5-nitroquinoline
  参考文献：
  名称：

  430. 4-羟基-和4-氯-3-甲基喹啉的硝化

  摘要：

  DOI：

  10.1039/jr9500002092

文献信息

• Intermediates for making N-aryl and N-heteroarylamide and urea
  申请人：Pfizer Inc.

  公开号：US05362878A1

  公开（公告）日：1994-11-08

  Compounds of the formula ##STR1## wherein R.sup.21 and R.sup.22 are as defined in the specification which are intermediates useful in the preparation of compounds of the formula ##STR2## and the pharmaceutically acceptable salts thereof, wherein Q and R.sup.1 are as defined in the specification. The compounds of formula I are inhibitors of acyl coenzyme A: cholesterol acyltransferase (ACAT) and are useful as hypolipidemic and antiatherosclerosis agents.

  式为## STR1##的化合物，其中R.sup.21和R.sup.22如规范中定义，这些化合物是制备式为## STR2##及其药学上可接受的盐的中间体，其中Q和R.sup.1如规范中定义。式I的化合物是酰辅酶A：胆固醇酰基转移酶（ACAT）的抑制剂，并且可用作降脂和抗动脉粥样硬化剂。
• New N-aryl and N-heteroarylamide and urea derivatives as inhibitors of acyl coenzyme A: cholesterol acyl transferase
  申请人：PFIZER INC.

  公开号：EP0418071A2

  公开（公告）日：1991-03-20

  Compounds of the formula the pharmaceutically acceptable salts thereof, wherein Q and R¹ are as defined below, and novel carboxylic acid and acid halide intermediates used in the synthesis of such compounds. The compounds of formula I are inhibitors of acyl coenzyme A: cholesterol acyltransferase (ACAT) and are useful as hypolipidemic and antiatherosclerosis agents.

  式中的化合物 其药学上可接受的盐，其中 Q 和 R¹ 如下文所定义，以及用于合成此类化合物的新型羧酸和酸卤化物中间体。式 I 的化合物是酰基辅酶 A：胆固醇酰基转移酶（ACAT）的抑制剂，可用作降血脂药和抗动脉粥样硬化药。
• New N-heteroarylamide derivatives as inhibitors of acyl coenzyme A: cholestrol acyl transferase
  申请人：PFIZER INC.

  公开号：EP0609960A1

  公开（公告）日：1994-08-10

  Compounds of the formula the pharmaceutically acceptable salts thereof, wherein Q is a substituted pyridine or pyrimidine group and R¹ incorporates a hydrocarbon group of from 4 to 16 carbon atoms, are inhibitors of acyl coenzyme A: cholesterol acyltransferase (ACAT) and are useful as hypolipidemic and antiatherosclerosis agents.

  式中的化合物 其中 Q 是取代的吡啶或嘧啶基团，R¹ 包含 4 至 16 个碳原子的烃基，是酰基辅酶 A：胆固醇酰基转移酶（ACAT）的抑制剂，可用作降血脂药和抗动脉粥样硬化药。
• Hypoxia-selective antitumor agents. 6. 4-(Alkylamino)nitroquinolines: a new class of hypoxia-selective cytotoxins
  作者：William A. Denny、Graham J. Atwell、Peter B. Roberts、Robert F. Anderson、Maruta Boyd、Colin J. L. Lock、William R. Wilson

  DOI：10.1021/jm00104a008

  日期：1992.12

  A series of isomeric 4-[[3-(dimethylamino)propyl]amino]nitroquinolines has been synthesized and evaluated as hypoxia-selective cytotoxins and as radioeensitizers of hypoxic cells. The compounds showed widely-differing hypersensitivity factors (ratios of cytotoxicity against wild-type and repair-deficient mammalian cells). Many compounds showed oxygen-sensitive bioreduction resulting in DNA alkylation, while others show oxygen-insensitive modes of action. Of the nitro isomers studied, the 5-nitro showed the greatest hypoxic selectivity. A series of ring-substituted analogues were then prepared, in an effort to lower its reduction potential of -286 mV. Structure-activity studies showed that the effects of substitution on reduction potential were complex, being mediated by electronic and steric effects on the nitro group, as well as by effects on quinoline pK(a). Two compounds of lower reduction potential, the 3- and 8-methyl analogues, showed improved selectivity (47- and 60-fold in a clonogenic assay). These two compounds also showed the highest ''in vitro therapeutic indices'' of the series as hypoxic cell radiosensitizers. Despite these favorable in vitro properties, neither compound had activity against hypoxic cells in SCCVII tumors when administered at 60% of the MTD.
• US5362878A
  申请人：——

  公开号：US5362878A

  公开（公告）日：1994-11-08