5-chloro-6-methoxyquinaldine | 882159-11-7

• 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: 5-chloro-6-methoxyquinaldine
• 英文别名: 5-chloro-6-methoxy-2-methylquinoline
• CAS: 882159-11-7
• 化学式: C₁₁H₁₀ClNO
• 分子量: 207.659
• InChiKey: RURKYENOQRQKHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-6-methoxyquinaldine 在 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 (3R,3aS,4S,4aR,8aS,9aR)-4-[(E)-2-(5-chloro-6-methoxyquinolin-2-yl)ethenyl]-3-methyl-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-3H-benzo[f][2]benzofuran-1-one
  参考文献：
  名称：

  发现和合成一系列新颖的基于喹啉的凝血酶受体（PAR-1）拮抗剂。

  摘要：

  描述了一系列结构新颖的高效凝血酶受体（PAR-1）拮抗剂的设计，合成和SAR研究。化合物30是一种高效的凝血酶受体拮抗剂（IC（50）= 6.3 nM），一种相关的化合物36在猴离体研究中显示出功效。

  DOI：

  10.1016/j.bmcl.2005.12.042
• 作为产物：
  描述：

  6-甲氧基-2-甲基喹啉 在 草酰氯 、 吩恶噻 10-氧化物 、 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 以86 %的产率得到5-chloro-6-methoxyquinaldine
  参考文献：
  名称：

  亲电氯锍区域选择性有机催化芳烃一氯化

  摘要：

  该手稿提出了芳烃的区域选择性氯化，几乎完全产生一氯化产物。它可耐受游离羟基、1°、2° 和 3° 胺、羧酸、其他极性和非极性官能团以及单取代和多取代的芳环。此外，还证明了使用氯锍盐作为氯化剂。该方法是作为其他必须从反应混合物中分离有机副产物的工艺的替代方案。此外，主要副产物是气态物质，例如CO和CO 2。该出版物介绍了亚砜、草酰氯和过氧化氢水溶液作为氯化混合物的应用。

  DOI：

  10.1002/adsc.202300971

文献信息

• AROYLQUINOLINE COMPOUNDS
  申请人：Liou Jing-Ping

  公开号：US20110275643A1

  公开（公告）日：2011-11-10

  A serious of nitro heterocyclic derivatives including a structure of formula (I) are provided. In formula (I), P, Q and R1 to R8 are defined in the specification. The derivatives disclosed in the present invention are characterized in inhibiting tubulin polymerization, and treating cancers and other tubulin polymerization-related disorders with a suitable pharmaceutical acceptable carrier.

  提供了一系列含有结构式（I）的硝基杂环衍生物。在结构式（I）中，P、Q和R1至R8在说明书中有定义。本发明揭示的衍生物具有抑制微管聚合的特性，并可使用合适的药用载体治疗癌症和其他与微管聚合有关的疾病。
• The Use of Sodium Chlorate/Hydrochloric Acid Mixtures as a Novel and Selective Chlorination Agent
  作者：Byung-Seok Moon、Han-Young Choi、Hun-Yeong Koh、Dae-Yoon Chi

  DOI：10.5012/bkcs.2011.32.2.472

  日期：2011.2.20

  Sodium chlorate/hydrochloric acid mixtures were used to chlorinate activated arenes and the $\alpha$-position of ketones. This chlorination method was used to produce selectively mono-, di-, and trichlorinated compounds by controlling the molarity of sodium chlorate. This reagent proved to be much more efficient and easier to handle than chlorine gas.

  氯酸钠/盐酸混合物被用于对活化芳烃和酮的α位进行氯化。通过控制氯酸钠的浓度，这种氯化方法能够选择性地生成单氯化、双氯化和三氯化化合物。这种试剂比氯气更有效且更易于操作。
• 5-Amino-2-aroylquinolines as Highly Potent Tubulin Polymerization Inhibitors. Part 2. The Impact of Bridging Groups at Position C-2
  作者：Hsueh-Yun Lee、Jang-Yang Chang、Chih-Ying Nien、Ching-Chuan Kuo、Kuang-Hsing Shih、Chun-Hsein Wu、Chi-Yen Chang、Wen-Yang Lai、Jing-Ping Liou

  DOI：10.1021/jm201031f

  日期：2011.12.22

  A variety of studies on the modification of combretastatin A-4 triggered our interest in the impact of the linkers between the 3,4,5-trimethoxyphenyl ring and 5-amino-6-methoxyquinoline on biological activity. The replacement of the carbonyl group with bond, amine, ether, sulfide, and sulfone groups was evaluated in this study. The results showed that compounds 14 and 15 containing sulfide and sulfone groups between the 3,4,5-trimethoxyphenyl ring (A-ring) and 5-amino-6-methoxyquinoline exhibited substantial antiproliferative activity against KB, HT29, and MKN45 cells with mean IC50 values of 42 and 12 nM, respectively. 15 inhibited the tubulin polymerization with an IC50 value of 2.0 mu M, similar to that with CA4. The continued work on the C-5 substituents of 3',4',5'-trimethoxybenzoyl-6-methoxyquinoline derivatives demonstrated that compound 7 possessing OH at C-5 exhibited excellent antiproliferative activity with mean IC50 values of 3.4 nM and microtubule destabilizing potency with an IC50 of 1.5 mu M, comparable to that of CA4 (IC50 = 1.9 mu M). It also exhibited substantial vascular disrupting effects. Compounds 7 and 15 exhibited significant efficacy against MDR/MRP-related drug-resistant cell lines (KB-vin10, KB-S15, and KB-7D) with mean IC50 values of 6.7 and 2.6 nM, respectively.
• AL-SHAAR, ADNAN H. M.;GILMOUR, DAVID W.;LYTHGOE, DAVID J.;MCCLENAGHAN, IA+, J. CHEM. SOC. PERKIN TRANS. PT 1,(1988) N1, C. 3019-3023
  作者：AL-SHAAR, ADNAN H. M.、GILMOUR, DAVID W.、LYTHGOE, DAVID J.、MCCLENAGHAN, IA+

  DOI：——

  日期：——
• Discovery and synthesis of a novel series of quinoline-based thrombin receptor (PAR-1) antagonists
  作者：Martin C. Clasby、Samuel Chackalamannil、Michael Czarniecki、Dario Doller、Keith Eagen、William J. Greenlee、Yan Lin、Hsingan Tsai、Yan Xia、Ho-Sam Ahn、Jacqueline Agans-Fantuzzi、George Boykow、Madhu Chintala、Carolyn Foster、Matthew Bryant、Janice Lau

  DOI：10.1016/j.bmcl.2005.12.042

  日期：2006.3

  The design, synthesis, and SAR studies of a structurally novel series of highly potent thrombin receptor (PAR-1) antagonists are described. Compound 30 is a highly potent thrombin receptor antagonist (IC(50)=6.3 nM), a related compound 36 showing efficacy in a monkey ex vivo study.

  描述了一系列结构新颖的高效凝血酶受体（PAR-1）拮抗剂的设计，合成和SAR研究。化合物30是一种高效的凝血酶受体拮抗剂（IC（50）= 6.3 nM），一种相关的化合物36在猴离体研究中显示出功效。