1,8-萘胺磺酸钾盐 | 16619-06-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,8-萘胺磺酸钾盐
• 英文名称: 1,8-naphthyl amine sulphonic acid potassium salt
• 英文别名: potassium 8-aminonaphthalene-1-sulfonate；8-amino-naphthalene-1-sulfonic acid ; potassium salt；8-Amino-naphthalin-1-sulfonsaeure; Kaliumsalz；potassium;8-aminonaphthalene-1-sulfonate
• CAS: 16619-06-0
• 化学式: C₁₀H₈NO₃S*K
• 分子量: 261.343
• InChiKey: SLHOJVAKQCSONM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.67
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,8-萘胺磺酸钾盐 在 sodium hydride 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-(5-[4-((2S)-2-[di(ethylsulfanyl)methyl]tetrahydro-1H-1-pyrrolyl)carbonyl-2-methoxy-5-nitrophenoxy]pentyl)-1,2-dihydro-1λ(6)-naphtho[1,8-cd]isothiazole-1,1-dione
  参考文献：
  名称：

  Design and synthesis of benzo[c,d]indolone-pyrrolobenzodiazepine conjugates as potential anticancer agents

  摘要：

  A series of benzo[c,d]indol-2(1H)one-PBD conjugates (11a-I) have been designed and synthesized as potential anticancer agents. These compounds were prepared by linking the C8-position of DC-81 with a benzo[c,d]indol-2(1H)one moiety through different alkane spacers in good yields and confirmed by H-1 NMR, mass and HRMS data. The DNA binding ability of these conjugates was evaluated by thermal denaturation studies and interestingly, compound 111 showed enhanced DNA binding ability. These compounds were also evaluated for their anticancer activity in selected human cancer cell lines of lung, skin, colon and prostate by using MTT assay method. These new conjugates showed promising anticancer activity with IC50 values ranging from 1.05 to 36.49 mu M. Moreover, cell cycle arrest in SubG1 phase was observed upon treatment of A549 cells with 1 and 2 mu M (IC50) concentrations of compound 111 and it induced apoptosis. This is confirmed by Annexin V-FITC, Hoechst staining, caspase-3 activity as well as DNA fragmentation analysis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.003

文献信息

• General synthetic approach towards annelated 3a,6-epoxyisoindoles by tandem acylation/IMDAF reaction of furylazaheterocycles. Scope and limitations
  作者：Fedor I. Zubkov、Eugenia V. Nikitina、Timur R. Galeev、Vladimir P. Zaytsev、Victor N. Khrustalev、Roman A. Novikov、Daria N. Orlova、Alexey V. Varlamov

  DOI：10.1016/j.tet.2014.01.008

  日期：2014.2

  investigated. The obtained Diels–Alder adducts are attractive and useful substrates for further transformations. Fused isoindoles can be prepared from them in one-step by aromatization of the 7-oxabicyclo[2.2.1]heptene ring. Other transformations, including halogenation, ring cleavage, and Wagner–Meerwein skeletal rearrangement, are also demonstrated. The spatial structures of the obtained compounds have

  提出了与恶嗪，恶唑，噻嗪，噻唑，嘧啶片段及其苯甲酰化类似物退火的3,6a-环氧异吲哚的一种有效且通用的一锅合成方法。该方法基于α，β-不饱和酸酐与α-呋喃基取代的氮杂杂环之间的串联N-酰化/分子内环加成反应（呋喃的分子内Diels-Alder反应，IMDAF）。后者可通过将各种糠醛与1,2-或1,3-N，X-双亲核试剂（氨基醇，氨基硫醇，二胺）缩合而轻松制备。观察到的IMDAF反应是立体选择性的：仅在非对映异构体之一普遍存在的情况下才形成外加合物。在大多数情况下，缩合/ N-酰化/ IMDAF反应顺序可以通过一锅多米诺协议进行。对该方法的范围和局限性进行了彻底的研究。所获得的Diels–Alder加合物是诱人且有用的底物，可用于进一步转化。熔融异吲哚可通过将7-氧杂双环[2.2.1]庚烯环芳构化而一步一步制得。还显示了其他转化，包括卤化，环裂解和Wagner-Meerwein骨架重排。通过
• Dannerth, Journal of the American Chemical Society, 1907, vol. 29, p. 1320
  作者：Dannerth

  DOI：——

  日期：——