4-chloro-8-methyl-7-nitroquinoline | 145363-59-3

• 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-8-methyl-7-nitroquinoline
• 英文别名: Quinoline, 4-chloro-8-methyl-7-nitro-
• CAS: 145363-59-3
• 化学式: C₁₀H₇ClN₂O₂
• 分子量: 222.631
• InChiKey: HPSARDCGQFCOPM-UHFFFAOYSA-N

物化性质

• 沸点：
  358.3±37.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)

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-8-methyl-7-nitroquinoline 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 亚硝酸特丁酯 、 potassium carbonate 、 tin(ll) chloride 、 copper(ll) bromide 作用下， 以 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 4.0h， 生成 7-bromo-8-methyl-4-phenylquinoline
  参考文献：
  名称：

  PLATINUM COMPLEX, NITROGEN-CONTAINING BIDENTATE CHELATE, AND APPARATUS FOR PROVIDING VISIBLE EMISSION OR NEAR-INFRARED EMISSION

  摘要：

  提供的是一种铂配合物，其结构由式(I)表示：其中A1至A3各自独立地表示一个5-或6-成员的不饱和环，A3可以选择性地形成在A1和A2之间；X1、X2和X3各自独立地表示碳或氮；R1表示氢、取代或未取代的C1-C6烷基、—CF2H、—CFH2、取代或未取代的C6-C12芳基或—CmF2m+1，其中m为1至5的整数；R2和R3各自独立地表示氢、C1-C12烷基、取代或未取代的C1-C6烷氧基、取代或未取代的C6-C12芳基或—CnF2n+1，其中n为0至3的整数；p和q各自独立地表示1至2的整数；当p或q等于2时，两个R2或R3可以结合形成一个C3-C8芳香或含氮杂芳香环。

  公开号：

  US20220144870A1
• 作为产物：
  描述：

  8-methyl-7-nitro-4(1H)-quinolone-3-carboxylic acid 在 三氯氧磷 作用下， 以 various solvent(s) 为溶剂， 生成 4-chloro-8-methyl-7-nitroquinoline
  参考文献：
  名称：

  Hypoxia-selective antitumor agents. 6. 4-(Alkylamino)nitroquinolines: a new class of hypoxia-selective cytotoxins

  摘要：

  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.

  DOI：

  10.1021/jm00104a008

文献信息

• Symmetrical Bis-Quinolinium Compounds:  New Human Choline Kinase Inhibitors with Antiproliferative Activity against the HT-29 Cell Line
  作者：Rosario Sánchez-Martín、Joaquín M. Campos、Ana Conejo-García、Olga Cruz-López、Mónica Báñez-Coronel、Agustín Rodríguez-González、Miguel A. Gallo、Juan C. Lacal、Antonio Espinosa

  DOI：10.1021/jm049061o

  日期：2005.5.1

  substituent R(4). The corresponding QSAR equation was obtained for the whole set of compounds for the antiproliferative activity, the electronic parameter sigma(R) of R(4), the molar refractivity of R(8), and the lipophilic parameters clog P and pi(linker). The most potent antiproliferative agent so far described is 40 for which an IC(50) = 0.45 microM was predicted by the QSAR equation, while its experimental

  研究旨在建立定义40种双喹啉鎓化合物对胆碱激酶的抑制和抗增殖活性的构效关系。这些衍生物在喹啉鎓环的4位具有电子释放基团。发现酶促抑制作用与接头的大小密切相关，最合适的是3，3'-联苯部分。另一方面，针对HT-29癌细胞系的抗增殖活性受接头类型和取代基R（4）的影响较小。针对整个化合物的抗增殖活性，R（4）的电子参数sigma（R），R（8）的摩尔折射率以及亲脂性参数clog P和pi（连接子）获得了相应的QSAR方程。
• Synthesis and antibacterial activity of new 4-alkoxy, 4-aminoalkyl and 4-alkylthioquinoline derivatives
  作者：Marie-Gratia Kayirere、Abdallah Mahamoud、Jacqueline Chevalier、Jean-Claude Soyfer、Andrée Crémieux、Jacques Barbe

  DOI：10.1016/s0223-5234(99)80076-2

  日期：1998.1

  4-Alkoxy-8-methyl-7-nitroquinolines, 4-alkylamino-8-methyl-7-nitroquinolines, 4-alkoxy-2,8-dimethylquinolines, 4-alkylthioquinolines were prepared from 8-methyl-7-nitro-4-quinolone, 8-methyl-7-nitro-4-chloro-quinoline, 2,8-dimethyl-4-quinolone and 4-hydroxyquinoline used as starting material. Compounds were characterized from H-1 and C-13 NMR spectra. These drugs were tested against selected gram-, gram+ and mycobacteria strains. A promising activity was observed against Mycobacterium smegmatis. (C) Elsevier, Paris.
• 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.
• PLATINUM COMPLEX, NITROGEN-CONTAINING BIDENTATE CHELATE, AND APPARATUS FOR PROVIDING VISIBLE EMISSION OR NEAR-INFRARED EMISSION
  申请人：National Tsing Hua University

  公开号：US20220144870A1

  公开（公告）日：2022-05-12

  Provided is a platinum complex having a structure represented by formula (I): wherein A1 to A3 each independently represent a 5-membered or 6-membered unsaturated ring, A3 is optionally formed between A1 and A2; X 1 , X 2 , and X 3 each independently represent carbon or nitrogen; R 1 represents hydrogen, substituted or unsubstituted C 1 -C 6 alkyl, —CF 2 H, —CFH 2 , substituted or unsubstituted C 6 -C 12 aryl or —C m F 2m+1 , m is an integer of 1 to 5; R 2 and R 3 each independently represent hydrogen, C 1 -C 12 alkyl, substituted or unsubstituted C 1 -C 6 alkoxyl, substituted or unsubstituted C 6 -C 12 aryl, or —C n F 2n+1 , n is an integer of 0 to 3; p and q each independently represent an integer of 1 to 2; and when p or q is equal to 2, two R 2 's or R 3 's may join to form a C 3 -C 8 aromatic or nitrogen-containing heteroaromatic ring.

  提供的是一种铂配合物，其结构由式(I)表示：其中A1至A3各自独立地表示一个5-或6-成员的不饱和环，A3可以选择性地形成在A1和A2之间；X1、X2和X3各自独立地表示碳或氮；R1表示氢、取代或未取代的C1-C6烷基、—CF2H、—CFH2、取代或未取代的C6-C12芳基或—CmF2m+1，其中m为1至5的整数；R2和R3各自独立地表示氢、C1-C12烷基、取代或未取代的C1-C6烷氧基、取代或未取代的C6-C12芳基或—CnF2n+1，其中n为0至3的整数；p和q各自独立地表示1至2的整数；当p或q等于2时，两个R2或R3可以结合形成一个C3-C8芳香或含氮杂芳香环。