2-isocyanato-6-methoxynaphthalene | 250255-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-isocyanato-6-methoxynaphthalene
• CAS: 250255-92-6
• 化学式: C₁₂H₉NO₂
• 分子量: 199.209
• InChiKey: GPNIVUNEKZPLIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-isocyanato-6-methoxynaphthalene 在 吡啶 、 水 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 98.0h， 生成 N-(6-methoxynaphthalen-2-yl)methanesulfonamide
  参考文献：
  名称：

  Synthesis and cycloxygenase inhibitory properties of new naphthalene-methylsulfonamido, naphthalene-methylsulfonyl and tetrahydronaphthalen-methylsulfonamido compounds

  摘要：

  We synthesized a series of new naphthalene derivatives: naproxen- and 6-methoxy naphthalene acetic acid-like 1-5. In these compounds the carboxylic function, typical of the classical NSAIDs, was replaced by a methylsulfonamido (1, 2 and 6a-c) or methylsulfonyl (3-5) group present in some selective COX-2 inhibitors. We also synthesized compounds 7 and 8 in which the naphthalene portion was substituted by tetrahydronaphthalene ring. Some of the new compounds were assayed for their enzymatic inhibitory activity towards cycloxygenase enzymes. Compounds 4 and 6b, at a concentration of 10 mu M exhibit percentage inhibition values of 65%, 50% and 29%, 87% towards COX-2 and COX-1, respectively. The substitution of carboxylic group with a mehylsulfonamido or a methylsulfonyl groups does not allow to direct the selectivity versus to cycloxygenase enzymes.

  DOI：

  10.3109/14756366.2014.940937
• 作为产物：
  描述：

  6-Methoxy-naphthalene-2-carbonyl azide 以 苯 为溶剂， 生成 2-isocyanato-6-methoxynaphthalene
  参考文献：
  名称：

  Diarylsemicarbazones: synthesis, antineoplastic activity and topoisomerase I inhibition assay

  摘要：

  A series of diarylsemicarbazones was synthesized and tested against human neoplastic cell lines. The more active members have a 1-naphthyl ring at the carbamidic nitrogen, and chloro, dimethylamino or nitro group substituents at the benzylidene moiety. None of these showed affinity to DNA. One of the more active compounds was tested as a topoisomerase I inhibitor and showed a potent effect. SAR studies demonstrated linear correlation between lypophilicity and activity on the most sensitive lines and a definite conformational shape for antineoplastic action. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00050-6

文献信息

• Phorbasides A−E, Cytotoxic Chlorocyclopropane Macrolide Glycosides from the Marine Sponge <i>Phorbas</i> sp. CD Determination of <i>C</i>-Methyl Sugar Configurations
  作者：John B. MacMillan、Guang Xiong-Zhou、Colin K. Skepper、Tadeusz F. Molinski

  DOI：10.1021/jo702307t

  日期：2008.5.1

  cytotoxic macrolide glycosides phorbasides A−E (3−7), each possessing a macrolide ring appended to a rare ene-yne-trans-2-chlorocyclopropane, were isolated from the same Western Australian sponge (Phorbas sp.) that provided phorboxazoles A and B. The structures of 3–7 were solved by analysis of spectroscopic data including NMR, MS, and CD. A synthesis of methyl 2-O-methyl-α-l-evalose from l-rhamnose

  五个新的大环内酯的细胞毒性苷phorbasides A-E（3 - 7），每个具有附加到一个罕见烯yne-一个大环内酯环的反式-2-氯环丙烷，由相同的西澳大利亚海绵分离（Phorbas所提供phorboxazoles属）的A和B结构3 - 7通过光谱数据，包括NMR，MS，和CD的分析来解决。的合成2- ø -甲基- α-升-evalose从升鼠李糖已经完成，并用于在糖残基的构型分配3。酸催化甲醇分解3然后对释放的O-甲基糖苷进行两步衍生化，得到附近的4- O-萘甲酰基/叔3- N-（2-氨基萘基）氨基甲酸酯衍生物，该化合物的激子偶联CD与由合成的1制备的衍生物具有相同的激子偶联CD。 2 - O-二甲基-α - 1-戊糖。