2-chloro-3-(quinolin-8-ylamino)naphthalene-1,4-dione | 22295-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-3-(quinolin-8-ylamino)naphthalene-1,4-dione
• 英文别名: 2-Chloro-3-(quinolin-8-ylamino)naphthalene-1,4-dione
• CAS: 22295-53-0
• 化学式: C₁₉H₁₁ClN₂O₂
• 分子量: 334.762
• InChiKey: MDNVZQJBWQOPPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 8-氨基喹啉 以 乙醇 为溶剂， 反应 16.0h， 以47.52%的产率得到2-chloro-3-(quinolin-8-ylamino)naphthalene-1,4-dione
  参考文献：
  名称：

  [EN] COMPOUNDS AND PHARMACEUTICAL COMPOSITION ASSOCIATED WITH UBIQUITINATION-PROTEASOME SYSTEM
  [FR] COMPOSÉS ET COMPOSITION PHARMACEUTIQUE ASSOCIÉE AU SYSTÈME D'UBIQUITINATION-PROTÉASOME

  摘要：

  该发明涉及一种新的化合物，具有低细胞毒性，用于阻断疾病中的泛素化-蛋白酶体系统。因此，这些化合物可用于治疗包括但不限于癌症、神经退行性疾病、炎症性疾病、自身免疫性疾病和代谢性疾病在内的各种疾病。

  公开号：

  WO2017020030A1

文献信息

• [EN] COMPOUNDS AND PHARMACEUTICAL COMPOSITION ASSOCIATED WITH UBIQUITINATION-PROTEASOME SYSTEM<br/>[FR] COMPOSÉS ET COMPOSITION PHARMACEUTIQUE ASSOCIÉE AU SYSTÈME D'UBIQUITINATION-PROTÉASOME
  申请人：UNIV TAIPEI MEDICAL

  公开号：WO2017020030A1

  公开（公告）日：2017-02-02

  The invention relates to new compounds with low cytotoxicity for blocking ubiquitination- proteasome system in diseases. Accordingly, these compounds can be used in treatment of treating disorders including, but not limited to, cancers, neurodegenerative diseases, inflammatory disorders and autoimmune disorders and metabolic disorders.

  该发明涉及一种新的化合物，具有低细胞毒性，用于阻断疾病中的泛素化-蛋白酶体系统。因此，这些化合物可用于治疗包括但不限于癌症、神经退行性疾病、炎症性疾病、自身免疫性疾病和代谢性疾病在内的各种疾病。
• Compounds and pharmaceutical composition associated with ubiquitination-proteasome system
  申请人：CALGENT BIOTECHNOLOGY CO., LTD.

  公开号：US10745350B2

  公开（公告）日：2020-08-18

  The invention relates to new compounds with low cytotoxicity for blocking ubiquitination-proteasome system in diseases. Accordingly, these compounds can be used in treatment of treating disorders including, but not limited to, cancers, neurodegenerative diseases, inflammatory disorders and autoimmune disorders and metabolic disorders.

  本发明涉及用于阻断疾病中泛素化-蛋白酶体系统的低细胞毒性新化合物。因此，这些化合物可用于治疗各种疾病，包括但不限于癌症、神经退行性疾病、炎症性疾病、自身免疫性疾病和代谢性疾病。
• TW2018/5267
  申请人：——

  公开号：——

  公开（公告）日：——
• COMPOUNDS AND PHARMACEUTICAL COMPOSITION ASSOCIATED WITH UBIQUITINATION-PROTEASOME SYSTEM
  申请人：Bridgent Biotechnology Inc.

  公开号：EP3328368B1

  公开（公告）日：2020-07-15
• Synthesis, anticancer activity and QSAR study of 1,4-naphthoquinone derivatives
  作者：Veda Prachayasittikul、Ratchanok Pingaew、Apilak Worachartcheewan、Chanin Nantasenamat、Supaluk Prachayasittikul、Somsak Ruchirawat、Virapong Prachayasittikul

  DOI：10.1016/j.ejmech.2014.07.024

  日期：2014.9

  A series of 2-substituted amino-3-chloro-1,4-naphthoquinone derivatives (3-12) were synthesized as anticancer agents and tested against four cancer cell lines including HepG2, HuCCA-1, A549 and MOLT-3. The most potent cytotoxic activity against the HepG2, HuCCA-1 and A549 cell lines was found to be m-acetylphenylamino-1,4-naphthoquinone (8) affording IC50 values of 4.758, 2.364 and 12.279 μM, respectively. On the other hand, p-acetylphenylamino-1,4-naphthoquinone (9) exhibited the most potent cytotoxic activity against the MOLT-3 cell line with an IC50 of 2.118 μM. Quantitative structure-activity relationship (QSAR) investigations provided good predictive performance as observed from cross-validated R of 0.9177-0.9753 and RMSE of 0.0614-0.1881. The effects of substituents at the 2-amino position on the naphthoquinone core structure and its corresponding influence on the cytotoxic activity were investigated by virtually constructing additional 1,4-naphthoquinone compounds (13-36) for which cytotoxic activities were predicted using equations obtained from the previously constructed QSAR models. Interpretation of informative descriptors from QSAR models revealed pertinent knowledge on physicochemical properties governing the cytotoxic activities of tested cancer cell lines. It is anticipated that the QSAR models developed herein could provide guidelines for further development of novel and potent anticancer agents.