4,6-二氯-3-(2-氯乙基)-2-甲基喹啉 | 57521-14-9

• 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
• 中文名称: 4,6-二氯-3-(2-氯乙基)-2-甲基喹啉
• 英文名称: 4,6-dichloro-3-(2-chloro-ethyl)-2-methyl-quinoline
• 英文别名: 4,6-Dichlor-3-(2-chlor-aethyl)-2-methyl-chinolin；3-(2-chloroethyl)-4,6-dichloro-2-methylquinoline；4,6-Dichloro-3-(2-chloroethyl)-2-methylquinoline
• CAS: 57521-14-9
• 化学式: C₁₂H₁₀Cl₃N
• 分子量: 274.577
• InChiKey: UWRNWBVHBOCMTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  4,6-二氯-3-(2-氯乙基)-2-甲基喹啉 在 溶剂黄146 作用下， 反应 5.0h， 以95.6%的产率得到8-chloro-4-methyl-2,3-dihydro-furo[3,2-c]quinoline
  参考文献：
  名称：

  Potential antineoplastics. Synthesis and cytotoxicity of certain 4-chloro-3-(2-chloroethyl)-2-methylquinolines and related derivatives

  摘要：

  In an extension of our work in the field of nitrogen heterocycles with potential cytotoxic activity, the synthesis of some substituted 4-chloro-3-(2-chloroethyl)-2-methylquinolines (10-13) from their parent 3-[1-(phenylamino)ethylidene]-dihydro-2(3H)furanones (6-9) is reported. The conversion of 10-13 to some thieno-, furo- and pyrrolo[3,2-c]quinolines (14-27, 31-33) is also described. The compounds were evaluated for their toxicity in brine shrimp (Artemia salina), and their cytotoxicity against some clinically isolated human tumors in vitro. Several compounds exhibited good toxic activity against Artemia salina, while the furanone (6, NSC 680781) displayed good antineoplastic activity and high selectivity against some cell lines from leukemia, lung cancer, colon and melanoma panels. This compound has been selected by the NCI for further testing in a new in vivo anticancer hollow fiber assay.

  DOI：

  10.1016/s0223-5234(99)80067-1
• 作为产物：
  描述：

  (3E)-3-[1-(4-chloroanilino)ethylidene]oxolan-2-one 在 三氯氧磷 作用下， 反应 4.0h， 以94.7%的产率得到4,6-二氯-3-(2-氯乙基)-2-甲基喹啉
  参考文献：
  名称：

  Potential antineoplastics. Synthesis and cytotoxicity of certain 4-chloro-3-(2-chloroethyl)-2-methylquinolines and related derivatives

  摘要：

  In an extension of our work in the field of nitrogen heterocycles with potential cytotoxic activity, the synthesis of some substituted 4-chloro-3-(2-chloroethyl)-2-methylquinolines (10-13) from their parent 3-[1-(phenylamino)ethylidene]-dihydro-2(3H)furanones (6-9) is reported. The conversion of 10-13 to some thieno-, furo- and pyrrolo[3,2-c]quinolines (14-27, 31-33) is also described. The compounds were evaluated for their toxicity in brine shrimp (Artemia salina), and their cytotoxicity against some clinically isolated human tumors in vitro. Several compounds exhibited good toxic activity against Artemia salina, while the furanone (6, NSC 680781) displayed good antineoplastic activity and high selectivity against some cell lines from leukemia, lung cancer, colon and melanoma panels. This compound has been selected by the NCI for further testing in a new in vivo anticancer hollow fiber assay.

  DOI：

  10.1016/s0223-5234(99)80067-1

文献信息

• TOPICAL FORMULATIONS
  申请人：BECK Petra Helga

  公开号：US20100093691A1

  公开（公告）日：2010-04-15

  There is provided topical pharmaceutical compositions comprising compounds of formula I wherein R 1 , R 2 , R 3 and X have meanings given in the description. These compositions can be used to treat microbial infections and to kill clinically latent microorganisms.

  提供了一种含有I式化合物的局部制药组合物，其中R1、R2、R3和X的含义在说明中给出。这些组合物可用于治疗微生物感染并杀死临床潜伏微生物。
• USE OF PYRROLOQUINOLINE COMPOUNDS TO KILL CLINICALLY LATENT MICROORGANISMS
  申请人：Beck Petra Helga

  公开号：US20120231995A1

  公开（公告）日：2012-09-13

  There is provided the use of compounds of formula I wherein R 1 , R 2 , R 3 and X have meanings given in the description, for the preparation of a medicament for killing clinically latent microorganisms. There is also provided the use of compounds of formula I for treating microbial infections, as well as certain compounds of formula I per se.

  提供了使用式子I中的化合物，其中R1、R2、R3和X的含义在说明中给出，用于制备杀死临床潜伏微生物的药物。还提供了使用式子I中的化合物治疗微生物感染的方法，以及某些式子I中的化合物本身。
• Raja, T K; Muthuvijayan, G; Reddy, P A, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 4, p. 270 - 272
  作者：Raja, T K、Muthuvijayan, G、Reddy, P A、Lakshmanan, J、Divakar, R

  DOI：——

  日期：——
• Ozawa et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 1407,1409
  作者：Ozawa et al.

  DOI：——

  日期：——
• US8207187B2
  申请人：——

  公开号：US8207187B2

  公开（公告）日：2012-06-26