N-(3-chloropropyl)naphthalen-1-amine | 500775-71-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(3-chloropropyl)naphthalen-1-amine
• CAS: 500775-71-3
• 化学式: C₁₃H₁₄ClN
• 分子量: 219.714
• InChiKey: IEXOHBRCCVLCAY-UHFFFAOYSA-N

物化性质

• 沸点：
  380.9±25.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(3-chloropropyl)naphthalen-1-amine 在 盐酸 、 potassium fluoride 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 (S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid 3-{9-[(Z)-ethylimino]-10-methyl-9H-benzo[a]phenoxazin-5-ylamino}-propyl ester; hydrochloride
  参考文献：
  名称：

  Functionalised benzo[a]phenoxazine dyes as long-wavelength fluorescent probes for amino acids

  摘要：

  A series of monoreactive functional benzo[a]phenoxazinium chlorides with a carboxyl, hydroxyl, amine or chloromethyl group were used as labels in the preparation of long-wavelength fluorescent amino acid bioconjugates. UV-visible and fluorescence studies of all compounds were carried out in ethanol and water at physiological pH. The absorption and emission of all compounds synthesised were in the range 555-640 nm and 632-681 nm, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.005
• 作为产物：
  描述：

  3-(naphthalen-1-ylamino)propan-1-ol 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以31%的产率得到N-(3-chloropropyl)naphthalen-1-amine
  参考文献：
  名称：

  Functionalised benzo[a]phenoxazine dyes as long-wavelength fluorescent probes for amino acids

  摘要：

  A series of monoreactive functional benzo[a]phenoxazinium chlorides with a carboxyl, hydroxyl, amine or chloromethyl group were used as labels in the preparation of long-wavelength fluorescent amino acid bioconjugates. UV-visible and fluorescence studies of all compounds were carried out in ethanol and water at physiological pH. The absorption and emission of all compounds synthesised were in the range 555-640 nm and 632-681 nm, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.005

文献信息

• Substituted Piperazines as Novel Potential Radioprotective Agents
  作者：Alzbeta Filipova、Jan Marek、Radim Havelek、Jaroslav Pejchal、Marcela Jelicova、Jana Cizkova、Martina Majorosova、Lubica Muckova、Tomas Kucera、Lukas Prchal、Miroslav Psotka、Natalie Zivna、Darja Koutova、Zuzana Sinkorova、Martina Rezacova、Ales Tichy

  DOI：10.3390/molecules25030532

  日期：——

  exposure underlines the need for novel radioprotective agents. Hence, a series of novel 1-(2-hydroxyethyl)piperazine derivatives were designed and synthesized. Some of the compounds protected human cells against radiation-induced apoptosis and exhibited low cytotoxicity. Compared to the previous series of piperazine derivatives, compound 8 exhibited a radioprotective effect on cell survival in vitro and

  辐射暴露风险的增加凸显了对新型辐射防护剂的需求。因此，设计并合成了一系列新型1-(2-羟乙基)哌嗪衍生物。一些化合物保护人体细胞免受辐射诱导的细胞凋亡，并表现出低细胞毒性。与之前的一系列哌嗪衍生物相比，化合物 8 在体外对细胞存活具有辐射防护作用，体内毒性较低。它还提高了全身照射后 30 天小鼠的存活率（尽管这种增加没有统计学意义）。总之，我们的体外和体内数据表明，我们的一些化合物作为潜在的辐射防护剂对于进一步研究很有价值。
• New NIR dyes based on quinolizino[1,9-hi]phenoxazin-6-iminium chlorides: synthesis, photophysics and antifungal activity
  作者：B. Rama Raju、Maria Inês P.S. Leitão、Maria João Sousa、Paulo J.G. Coutinho、M. Sameiro T. Gonçalves

  DOI：10.1016/j.dyepig.2019.107870

  日期：2020.2

  9-hi]phenoxazinium chlorides were evaluated against the yeast Saccharomyces cerevisiae in a broth microdilution assay. It was found that their antifungal activity depended on the substituent at 14-amino position in benzo[a]quinolizino[1,9-hi]phenoxazin-14(5H)-iminium chlorides, and also on the addition of a fused benzene ring, which occurs in naphtho[2,3-a]quinolizino[1,9-hi]phenoxazin-14(5H)-iminium chloride. The

  制备了一系列新的基于聚吲哚和萘-1-胺衍生物或蒽-1-胺的喹啉并[1,9- hi ]苯恶嗪鎓染料。这些喹啉并[1，9- hi ]苯恶嗪氯化物的N-末端含有芳族或脂族取代基，以及诸如氯，羟基和羧基的官能团。在酸性和碱性条件下，在无水乙醇和水性介质中研究了这些化合物的光物理行为。这些荧光团分别显示最大675 nm和712 nm的最大吸收和发射，可作为生物学测定中的替代传感工具。 在肉汤微量稀释试验中，针对酵母酿酒酵母评估了所有喹喔啉[1,9- hi ]苯氧嗪鎓氯化物。发现它们的抗真菌活性取决于苯并[ a ]喹啉并[1,9 - hi ]苯恶嗪-14（5 H）-亚胺氯化物中14-氨基位置的取代基，还取决于稠合苯环的添加。发生在萘并[2,3- a ]喹啉并[ 1,9 - hi ]苯恶嗪-14（5 H）-亚氯化亚胺中。苯并[ a ]喹啉并[1,9 - hi ]苯恶嗪-14（5 H）-在杂环核的14-氨基位置具有3-氯丙基取代基的氯化亚胺。
• Benzo[a]phenoxazinium chlorides: Synthesis, antifungal activity, in silico studies and evaluation as fluorescent probes
  作者：Maria Inês P.S. Leitão、B. Rama Raju、Nuno M.F.S.A. Cerqueira、Maria João Sousa、M. Sameiro T. Gonçalves

  DOI：10.1016/j.bioorg.2020.103730

  日期：2020.5

  other benzo[a]phenoxazinium chlorides. Minimum Inhibitory Concentration (MIC) values between 1.56 and >200 µM were observed. Fluorescence microscopy studies, used to assess the intracellular distribution of the dyes, showed that these benzo[a]phenoxazinium chlorides function as efficient and site specific probes for the detection of the vacuole membrane. The added advantage of some of the compounds

  合成了四种新的苯并[a]苯恶嗪氯化物，其氯化物，乙酯和甲基的组合作为氨基取代基的末端。对这些化合物进行了表征，并在无水乙醇和水中研究了它们的光学性质。在肉汤微量稀释试验中，与一系列其他36种苯并[a]苯恶嗪氯化物一起测试了它们对啤酒酵母的抗增殖活性。观察到最小抑菌浓度（MIC）值在1.56和> 200 µM之间。用于评估染料在细胞内分布的荧光显微镜研究表明，这些苯并[a]苯恶嗪氯化物可作为有效的和特定位置的探针来检测液泡膜。某些化合物的附加优点是显示出较低的MIC值，是内质网（ER）的液泡膜和核周膜同时染色。使用PDB上可用的晶体结构（代码1W6K）对人膜蛋白氧化角鲨烯环化酶（OSC）进行了分子对接研究。结果表明，这些最具活性的化合物在ER酶OSC的活性位点中具有更好的适应性，表明该酶是潜在的靶标。总体而言，结果表明，苯并[a]苯恶嗪氯化物是可替代市售染料的有趣替代品。这些化合物取代基的变
• Functionalised benzo[a]phenoxazine dyes as long-wavelength fluorescent probes for amino acids
  作者：Vânia H.J. Frade、Paulo J.G. Coutinho、João C.V.P. Moura、M. Sameiro T. Gonçalves

  DOI：10.1016/j.tet.2006.12.005

  日期：2007.2

  A series of monoreactive functional benzo[a]phenoxazinium chlorides with a carboxyl, hydroxyl, amine or chloromethyl group were used as labels in the preparation of long-wavelength fluorescent amino acid bioconjugates. UV-visible and fluorescence studies of all compounds were carried out in ethanol and water at physiological pH. The absorption and emission of all compounds synthesised were in the range 555-640 nm and 632-681 nm, respectively. (c) 2006 Elsevier Ltd. All rights reserved.