isopropyl 4-oxo-2-phenyl-1,4-dihydroquinoline-6-carboxylate | 90033-87-7

• 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: isopropyl 4-oxo-2-phenyl-1,4-dihydroquinoline-6-carboxylate
• 英文别名: propan-2-yl 4-oxo-2-phenyl-1H-quinoline-6-carboxylate
• CAS: 90033-87-7
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: IIZKQQGMBXFRNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氧代-2-苯基-1H-喹啉-6-羧酸 以 (2S)-N-methyl-1-phenylpropan-2-amine hydrate 为溶剂， 生成 isopropyl 4-oxo-2-phenyl-1,4-dihydroquinoline-6-carboxylate
  参考文献：
  名称：

  4-quinolone derivatives having anti-inflammatory, anti-allergic,

  摘要：

  本发明的4-喹诺酮衍生物具有抗炎、抗过敏、止咳、祛痰和抗血栓活性。本文描述了含有这些化合物和其药学上可接受的盐的药物组合物以及治疗人类和动物的方法。

  公开号：

  US04711898A1

文献信息

• 4(1H)-quinolone derivatives overcome acquired resistance to anti-microtubule agents by targeting the colchicine site of β-tubulin
  作者：Ming-Shiu Lin、Tse-Ming Hong、Ting-Hung Chou、Shuenn-Chen Yang、Wei-Chia Chung、Chia-Wei Weng、Mei-Ling Tsai、Ting-Jen Rachel Cheng、Jeremy J.W. Chen、Te-Chang Lee、Chi-Huey Wong、Rong-Jie Chein、Pan-Chyr Yang

  DOI：10.1016/j.ejmech.2019.111584

  日期：2019.11

  Developing new therapeutic strategies to overcome drug resistance of cancer cells is an ongoing endeavor. From among 2 million chemicals, we identified ethyl 4-oxo-2-phenyl-1,4-dihydroquinoline-6-carboxylate (AS1712) as a low-toxicity inhibitor of lung cancer cell proliferation and xenograft tumor growth. We show that AS1712 is active against broad cancer cell lines and is able to bind in the colchicine-binding

  开发新的治疗策略以克服癌细胞的耐药性是正在进行的努力。在200万种化学药品中，我们确定了4-氧代-2-苯基-1,4-二氢喹啉-6-羧酸乙酯（AS1712）是肺癌细胞增殖和异种移植肿瘤生长的低毒性抑制剂。我们显示，AS1712对广泛的癌细胞系具有活性，并且能够在β-微管蛋白的秋水仙碱结合口袋中结合，从而抑制微管装配，并因此诱导有丝分裂停滞和凋亡。我们基于细胞的结构-活性关系研究确定了一种新的先导化合物RJ-LC-15-8，它对H1975细胞的抗增殖能力比对AS1712的强，同时保持了相似的作用机理。尤其，AS1712和RJ-LC-15-8克服了P-糖蛋白外排泵和β-微管蛋白的改变，这些改变导致获得性抵抗癌细胞靶向微管的药物。AS1712和RJ-LC-15-8可能是克服了对癌细胞的微管靶向剂的后天抵抗力的先导化合物。
• 4(1H)-QUINOLONE DERIVATIVES AND USES THEREOF
  申请人：Academia Sinica

  公开号：US20200330449A1

  公开（公告）日：2020-10-22

  Compounds of Formula (I) and methods for treating, delaying, and/or preventing the adverse effects of proliferative diseases, such as cancers including, for example, lung cancer, breast cancer, ovarian cancer, prostate cancer, head cancer, neck cancer, head and neck cancer, or leukemia (e.g., cancer resistant to treatment by one or more microtubule-targeting agents, e.g., cancer resistant to multiple drugs associated with P-glycoprotein (P-gp) overexpression). Methods of inhibiting polymerization of a cancer cell microtubule in a subject in need thereof or a cell, tissue, or biological sample, binding p-tubulin, inhibiting microtubule assembly and, inducing apoptosis in a cancer cell resistant to multiple drugs in a tissue, biological sample, or subject. Pharmaceutical compositions, kits, and methods of using the compounds for treating any of the target diseases described herein.

  公式(I)的化合物及治疗、延迟和/或预防增生性疾病的不良影响的方法，例如癌症，包括肺癌、乳腺癌、卵巢癌、前列腺癌、头颈癌、头颈癌或白血病（例如，对一种或多种微管靶向药物治疗耐药的癌症，例如对P-糖蛋白（P-gp）过表达相关的多种药物治疗耐药的癌症）。抑制癌细胞微管聚合的方法，适用于需要的个体或细胞、组织或生物样本，结合p-微管蛋白，抑制微管组装，并在组织、生物样本或个体中诱导对多种药物耐药的癌细胞的凋亡。药物组合物、试剂盒和使用上述化合物治疗任何本文描述的靶疾病的方法。
• 4-Quinolone derivatives
  申请人：NIPPON SHINYAKU COMPANY, LIMITED

  公开号：EP0104959A1

  公开（公告）日：1984-04-04

  The present invention relates to 4-quinolone derivatives represented by the following general formula (I) and salts thereof, as well as their use as pharmaceuticals and methods for manufacturing them. In the formula, R' and R2 are same or different and they are hydrogen, lower aklyl of one to eight carbon chain length or lower alkenyl of one to four carbon chain length; R3 stands for hydrogen, lower alkyl of one to eight carbon chain length, lower alkyl of one to eight carbon chain length with one or two hydroxyl group(s), lower alkyl or three to ten carbon chain length with one or two ether bond(s), or-(CH2)nA where n is an integer of 1 to 3 and A is acetyl, acetyloxy, cyano orphenoxy; Z stands for phenyl with or without substituent(s) selected from a group consisting of hydrogen, halogen, lower alkyl of one to eight carbon chain length, lower haloalkyl of one to three carbon chain length, lower alkoxy of one to four carbon chain length and COOR4 (in which R4 is hydrogen or lower alkyl of one to four carbon chain length) or Z stands for unsaturated hetero ring radical with five or six members having nitrogen, oxygen or sulfur as hetero atom.

  本发明涉及以下通式(I)代表的4-喹啉酮衍生物及其盐，以及它们作为药物的用途和制造方法。 式中，R'和 R2 可相同或不同，它们分别为氢、1 至 8 个碳链长度的低级烷基或 1 至 4 个碳链长度的低级烯基；R3 代表氢、1 至 8 个碳链长度的低级烷基、1 至 8 个碳链长度的低级烷基且带有 1 或 2 个羟基、3 至 10 个碳链长度的低级烷基且带有 1 或 2 个醚键，或-(CH2)nA，其中 n 为 1 至 3 的整数，A 为乙酰基、乙酰氧基、氰基或苯氧基；Z 代表苯基，带有或不带有选自氢、卤素、1 至 8 个碳链长度的低级烷基、1 至 3 个碳链长度的低级卤代烷基、1 至 4 个碳链长度的低级烷氧基和 COOR4（其中 R4 为氢或 1 至 4 个碳链长度的低级烷基）的取代基，或 Z 代表不饱和杂环基，其五个或六个成员的杂原子为氮、氧或硫。
• ENOMOTO, HIROSHI;NOMURA, TADATOSHI;AOYAGI, YOSHIAKI;CHOKAI, SHOICHI;FUJIT+
  作者：ENOMOTO, HIROSHI、NOMURA, TADATOSHI、AOYAGI, YOSHIAKI、CHOKAI, SHOICHI、FUJIT+

  DOI：——

  日期：——
• US4711898A
  申请人：——

  公开号：US4711898A

  公开（公告）日：1987-12-08