9H-Xanthene-9-methanamine hydrochloride | 5101-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 9H-Xanthene-9-methanamine hydrochloride
• 英文别名: C-xanthen-9-yl-methylamine; hydrochloride；Xanthene-9-methylamine hydrochloride；9H-xanthen-9-ylmethanamine;hydrochloride
• CAS: 5101-81-5
• 化学式: C₁₄H₁₃NO*ClH
• 分子量: 247.724
• InChiKey: ACYQEHDIBOQLEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9H-Xanthene-9-methanamine hydrochloride 、 1-<4,6-bis(allylamino)-1,3,5-triazin-2-yl>-4-piperidone hydrochloride 在 盐酸 、 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 2,4-diallylamino-6-[4-(xanthen-9-ylmethylamino)-piperidin-1-yl]-1,3,5-triazine
  参考文献：
  名称：

  New triazine derivatives as potent modulators of multidrug resistance

  摘要：

  A series of 70 triazine derivatives have been synthesized and tested for their capacity to modulate multidrug resistance (MDR) in DC-3F/AD and KB-A1 tumor cells in vitro, in comparison with verapamil (VRP), a calcium channel antagonist currently used in therapy as an antihypertensive drug, which also shows MDR modulating activity. Among the 12 selected compounds, 16 (S9788) showed high MDR reversing properties in vitro (300- and 6-fold VRP at 5-mu-M in DC-3F/AD and KB-A1 cells, respectively) and induced a strong accumulation of adriamycin. The relationship between the increase of ADR accumulation and the fold reversal induced by these compounds and their lack of effects on the sensitive DC-3F cells suggest that they act mainly by inhibiting the P-glycoprotein (Pgp) catalyzed efflux of cytotoxic agents, as already described for a majority of MDR modulators. In vivo, in association with the antitumor drug vincristine (0.25 mg/kg), 16 (100 mg/kg) increased the TIC by 39% in mice bearing the resistant tumor cell line P388/VCR. According to these interesting properties, 16 was selected for a clinical development because it was more bioavailable than 34, even though it was less active.

  DOI：

  10.1021/jm00091a017
• 作为产物：
  描述：

  吨-9-碳乙酰胺 在 [(aNHC)KN(SiMe₃)₂]₂ 、 频那醇硼烷 、 水 、 sodium hydroxide 、 盐酸 作用下， 以 甲苯 、 乙醚 、 水 为溶剂， 反应 13.0h， 以42%的产率得到9H-Xanthene-9-methanamine hydrochloride
  参考文献：
  名称：

  使用基于NHC的异常钾络合物实现无过渡金属的伯酰胺催化还原：将亲核性与Lewis酸性活化相结合

  摘要：

  异常的基于N-杂环卡宾（aNHC）的钾络合物用作无过渡金属的催化剂，用于在环境条件下将伯酰胺还原为相应的伯胺。仅催化剂的2mol％负载显示出广泛的底物范围，包括具有优异的官能团耐受性的芳族，脂族和杂环伯酰胺。该方法适用于手性酰胺的还原，并用于克级的药学上有价值的前体的合成。在机理研究过程中，通过光谱技术分离和表征了几种中间体，并且通过单晶XRD表征了一种催化中间体。定义明确的催化剂和可分离的中间体，以及一些化学计量的原位实验 NMR实验和DFT研究帮助我们勾画出了该还原过程的机理途径，从而揭示了催化剂的双重作用，包括aNHC的亲核活化以及K离子的Lewis酸性活化。

  DOI：

  10.1039/c9sc05953a

文献信息

• Synthesis and Antitumor Activity of Some New 2-Chloroethylnitrosoureas
  作者：Evangelos Filippatos、Aspasia Papadaki-Valiraki、Christos Roussakis、Jean-Francois Verbist

  DOI：10.1002/ardp.19933260805

  日期：——

  The synthesis of a series of N‐(2‐chloroethyl)‐N′‐(9H‐xanthen‐9‐yl)‐N‐nitrosoureas and N‐(2‐chloroethyl)‐N′‐(9H‐thioxanthen‐9‐yl)‐N‐nitrosoureas is described. The title compounds were evaluated against NSCLCN6 L16 bronchial epidermoid carcinoma in vitro and some of them were found to be active. N‐(2‐chloroethyl)‐N′‐(2‐methoxy‐9H‐xanthen‐9‐yl)‐N‐nitrosourea (8e) was active against leukemia P388 tumor

  一系列N-(2-氯乙基)-N'-(9H-xanthen-9-基)-N-亚硝基脲和N-(2-氯乙基)-N'-(9H-噻吨-9-基)的合成) -N - 亚硝基脲类。标题化合物在体外针对 NSCLCN6 L16 支气管表皮样癌进行了评估，发现其中一些具有活性。N-(2-氯乙基)-N'-(2-甲氧基-9H-黄原酸-9-基)-N-亚硝基脲(8e)对小鼠白血病P388肿瘤系统有活性。