2-chloro-3-cyclopentylamino-1,4-naphthoquinone | 57097-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-chloro-3-cyclopentylamino-1,4-naphthoquinone
• 英文别名: 2-Chloro-3-(cyclopentylamino)naphthalene-1,4-dione
• CAS: 57097-67-3
• 化学式: C₁₅H₁₄ClNO₂
• 分子量: 275.735
• InChiKey: JAUMABDNQXOKAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-3-cyclopentylamino-1,4-naphthoquinone 在 硫酸 、 氢溴酸 作用下， 以 乙醇 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 5.5h， 生成 1-cyclopentyl-2-methyl-4,9-dioxo-3-(pyrazin-2-ylmethyl)-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-ium bromide
  参考文献：
  名称：

  Dioxonaphthoimidazolium 是具有 SOX2 抑制特性的强效和选择性流氓干细胞清除剂

  摘要：

  多能干细胞在再生医学方面具有独特的定位，但只有将其致瘤倾向与其多能特性脱钩，才能实现其临床潜力。使用小分子去除残留的未分化多能细胞，否则这些细胞会转化为畸胎瘤和畸胎瘤，与非药物方法相比具有几个优势。Dioxonapthoimidazolium YM155 是一种存活素抑制剂，可诱导未分化干细胞的选择性和强效细胞死亡。在此，对干细胞毒性的结构要求进行了研究，发现其与恶性细胞中细胞毒性所必需的结构要求密切相关。对醌和咪唑鎓部分的依赖性很大，但对环取代基的依赖性较小，主要用于微调活动。鉴定出几种有效的类似物，如 YM155，抑制干细胞中的 survivin 并降低 SOX2。SOX2 的减少会导致多能因子的不平衡，这可能会促使细胞分化，从而降低异常畸胎瘤形成的风险。由于 NF-κB p50 亚基的磷酸化也被抑制，磷酸化-p50、SOX2 和 survivin 之间的串扰可能暗示 NF-κB 信号

  DOI：

  10.1002/cmdc.201600262
• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 、 环戊胺 以 乙醇 为溶剂， 反应 18.0h， 生成 2-chloro-3-cyclopentylamino-1,4-naphthoquinone
  参考文献：
  名称：

  Dioxonaphthoimidazolium 是具有 SOX2 抑制特性的强效和选择性流氓干细胞清除剂

  摘要：

  多能干细胞在再生医学方面具有独特的定位，但只有将其致瘤倾向与其多能特性脱钩，才能实现其临床潜力。使用小分子去除残留的未分化多能细胞，否则这些细胞会转化为畸胎瘤和畸胎瘤，与非药物方法相比具有几个优势。Dioxonapthoimidazolium YM155 是一种存活素抑制剂，可诱导未分化干细胞的选择性和强效细胞死亡。在此，对干细胞毒性的结构要求进行了研究，发现其与恶性细胞中细胞毒性所必需的结构要求密切相关。对醌和咪唑鎓部分的依赖性很大，但对环取代基的依赖性较小，主要用于微调活动。鉴定出几种有效的类似物，如 YM155，抑制干细胞中的 survivin 并降低 SOX2。SOX2 的减少会导致多能因子的不平衡，这可能会促使细胞分化，从而降低异常畸胎瘤形成的风险。由于 NF-κB p50 亚基的磷酸化也被抑制，磷酸化-p50、SOX2 和 survivin 之间的串扰可能暗示 NF-κB 信号

  DOI：

  10.1002/cmdc.201600262

文献信息

• 미세조류 파괴용 조성물
  申请人：Industry-Academic Cooperation Foundation, Chosun University 조선대학교산학협력단(220050171903) BRN ▼408-82-13419

  公开号：KR101761848B1

  公开（公告）日：2017-07-26

  본 발명은 미세조류 파괴용 조성물에 관한 것으로, 더욱 자세하게는 특정 치환기를 가지는 나프토퀴논 화합물을 함유하는 미세조류 파괴용 조성물에 관한 것이다. 본 발명에 따른 신규한 미세조류 파괴용 조성물은 해양 미세조류 배양장 또는 녹조 또는 적조가 발생된 지역 또는 녹조나 적조 발생 예상 지역에 처리하여 녹조 및 적조 피해를 예방할 수 있는 효과가 있다.

  本发明涉及微藻破坏用配方，更具体地涉及含有特定取代基的萘酮化合物的微藻破坏用配方。根据本发明，新型微藻破坏用配方可在海洋微藻培养场或发生褐藻或红藻的区域或预计发生褐藻或红藻的区域进行处理，以预防褐藻和红藻的损害。
• [EN] NAPHTHAQUINONE METHYLTRANSFERASE INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE NAPHTAQUINONE MÉTHYLTRANSFÉRASE ET LEURS UTILISATIONS
  申请人：SLOAN KETTERING INST CANCER

  公开号：WO2015172076A1

  公开（公告）日：2015-11-12

  Provided herein are compounds of (I), and pharmaceutically acceptable salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, and prodrugs thereof. Also provided are pharmaceutical compositions and methods involving the inventive compounds for the treatment of proliferative diseases (e.g., cancer (e.g., leukemia, breast cancer, melanoma, metastatic cancer) and diseases associated with inappropriate SET8 activity. Also provided are methods for inhibiting SET8 and methods for labelling SET8.

  本文提供了化合物(I)及其药用可接受的盐、溶剂合物、水合物、多型体、共晶体、互变异构体、立体异构体和其前药。还提供了涉及创新化合物用于治疗增殖性疾病（例如，癌症（例如，白血病、乳腺癌、黑色素瘤、转移性癌症）和与不当的SET8活性相关的疾病）的药物组合物和方法。还提供了用于抑制SET8的方法和用于标记SET8的方法。
• Naphthoquinones
  申请人：Hoffmann-La Roche Inc.

  公开号：US03935246A1

  公开（公告）日：1976-01-27

  Compounds represented by the formula ##SPC1## Wherein R is a cyclopentyl or cycloheptyl and R.sub.1 is a hydrogen, halogen or lower alkoxy, Processes for their production and novel intermediates as well as therapeutic preparations containing the compounds as the active ingredient for amoebicidal or bacteriostatic treatment are disclosed.

  公式为## SPC1 ##的化合物，其中R为环戊基或环庚基，R.sub.1为氢、卤素或低烷氧基，公开了它们的生产过程和新颖的中间体，以及含有该化合物作为活性成分的抗阿米巴或细菌静止治疗的治疗制剂。
• Antiproliferative, DNA intercalation and redox cycling activities of dioxonaphtho[2,3-d]imidazolium analogs of YM155: A structure–activity relationship study
  作者：Si-Han Sherman Ho、Mei-Yi Sim、Wei-Loong Sherman Yee、Tianming Yang、Shyi-Peng John Yuen、Mei-Lin Go

  DOI：10.1016/j.ejmech.2015.09.026

  日期：2015.11

  The anticancer agent YM155 is widely investigated as a specific survivin suppressant. More recently, YM155 was found to induce DNA damage and this has raised doubts as to whether survivin is its primary target. In an effort to assess the contribution of DNA damage to the anticancer activity of YM155, several analogs were prepared and evaluated for antiproliferative activity on malignant cells, participation in DNA intercalation and free radical generation by redox cycling. The intact positively charged scaffold was found to be essential for antiproliferative activity and intercalation but was less critical for redox cycling where the minimal requirement was a pared down bicyclic quinone. Side chain requirements at the N-1 and N-3 positions of the scaffold were more alike for redox cycling and intercalation than antiproliferative activity, underscoring yet again, the limited structural overlaps for these activities. Furthermore, antiproliferative activities were poorly correlated to DNA intercalation and redox cycling. Potent antiproliferative activity (IC50 9-23 nM), exceeding that of YM155, was found for a minimally substituted methyl analog AB7. Like YM155 and other dioxonaphthoimidazoliums, AB7 was a modest DNA intercalator but with weak redox cycling activity. Thus, the capacity of this scaffold to inflict direct DNA damage leading to cell death may not be significant and YM155 should not be routinely classified as a DNA damaging agent. (C) 2015 Elsevier Masson SAS. All rights reserved.
• US3935246A
  申请人：——

  公开号：US3935246A

  公开（公告）日：1976-01-27