2-羟基-1-萘甲酰氯 | 38077-75-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-羟基-1-萘甲酰氯
• 中文别名: 2-羟基萘-1-羰酰氯
• 英文名称: 2-Hydroxy-naphthalene-1-carbonyl chloride
• 英文别名: 2-Hydroxynaphthalene-1-carbonyl chloride
• CAS: 38077-75-7
• 化学式: C₁₁H₇ClO₂
• 分子量: 206.628
• InChiKey: WBJWXIQDBDZMAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2-羟基-1-萘甲酸	2-hydroxy-1-naphthalenecarboxylic acid	2283-08-1	C11H8O3	188.183
  2-羟基-1-萘酸甲酯	methyl 2-hydroxy-1-naphthoate	947-65-9	C12H10O3	202.21

反应信息

• 作为反应物：
  描述：

  2-羟基-1-萘甲酰氯 在 sodium hydroxide 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  设计和合成醛糖还原酶的高效和选择性（2-芳基氨基甲酰基-苯氧基）-乙酸抑制剂，用于治疗慢性糖尿病并发症。

  摘要：

  最近鉴定慢性糖尿病并发症的治疗方法的努力导致发现了一系列新的高效和选择性的（2-芳基氨基甲酰基-苯氧基）乙酸醛糖还原酶抑制剂。化合物类别的特征是核心模板，该模板利用分子内氢键将药效基团的关键结构元件定位在构象中，从而促进了高结合亲和力。铅候选物，例如40，5-氟-2-（4-溴-2-氟-苄硫代氨基甲酰基）-苯氧基乙酸，抑制醛糖还原酶，IC（50）为30 nM，而对醛还原酶的活性低1100倍，是一种与活性醛解毒有关的酶。另外，实施例40在4天STZ诱导的糖尿病大鼠模型中以31mg / kg / d po的ED（50）降低了神经山梨糖醇水平。

  DOI：

  10.1016/j.bmc.2004.07.062
• 作为产物：
  描述：

  2-羟基-1-萘甲酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 正庚烷 为溶剂， 生成 2-羟基-1-萘甲酰氯
  参考文献：
  名称：

  设计和合成醛糖还原酶的高效和选择性（2-芳基氨基甲酰基-苯氧基）-乙酸抑制剂，用于治疗慢性糖尿病并发症。

  摘要：

  最近鉴定慢性糖尿病并发症的治疗方法的努力导致发现了一系列新的高效和选择性的（2-芳基氨基甲酰基-苯氧基）乙酸醛糖还原酶抑制剂。化合物类别的特征是核心模板，该模板利用分子内氢键将药效基团的关键结构元件定位在构象中，从而促进了高结合亲和力。铅候选物，例如40，5-氟-2-（4-溴-2-氟-苄硫代氨基甲酰基）-苯氧基乙酸，抑制醛糖还原酶，IC（50）为30 nM，而对醛还原酶的活性低1100倍，是一种与活性醛解毒有关的酶。另外，实施例40在4天STZ诱导的糖尿病大鼠模型中以31mg / kg / d po的ED（50）降低了神经山梨糖醇水平。

  DOI：

  10.1016/j.bmc.2004.07.062

文献信息

• Scaffold Diversity Inspired by the Natural Product Evodiamine: Discovery of Highly Potent and Multitargeting Antitumor Agents
  作者：Shengzheng Wang、Kun Fang、Guoqiang Dong、Shuqiang Chen、Na Liu、Zhenyuan Miao、Jianzhong Yao、Jian Li、Wannian Zhang、Chunquan Sheng

  DOI：10.1021/acs.jmedchem.5b00910

  日期：2015.8.27

  thio-evodiamine (66c) showed excellent in vitro and in vivo antitumor efficacy with good tolerability and low toxicity. Antitumor mechanism and target profiling studies indicate that compound 66c is the first-in-class triple topoisomerase I/topoisomerase II/tubulin inhibitor. Overall, this study provided an effective strategy for natural product-based drug discovery.

  基于天然产物的药物发现中的一个关键问题是如何将产物转化为具有最佳药理特性的类药物分子。天然产物启发的支架多样性的产生是一种有效但具有挑战性的策略，用于研究更广阔的化学空间并确定有前途的药物线索。将我们的工作扩展到天然产物evodiamine，设计并合成了一个包含11个evodiamine启发的新型支架及其衍生物的多样化文库。它们中的大多数显示出对各种人类癌细胞系的良好至优异的抗肿瘤活性。特别地，3-氯-10-羟基硫代吴茱萸碱（66C）显示出优异的体外和体内抗肿瘤功效，耐受性好，毒性低。抗肿瘤机制和靶标分析研究表明，化合物66c是同类中的第一个三重拓扑异构酶I /拓扑异构酶II /微管蛋白抑制剂。总的来说，这项研究为基于天然产物的药物发现提供了有效的策略。
• Novel rearrangement of 1,3-benzo(naphtho)dioxin-4(1)-ones under Vilsmeier-Haack reagent
  作者：Oleg K. Farat、Anton V. Kovtun、Svetlana A. Varenichenko、Aleksander V. Mazepa、Victor I. Markov

  DOI：10.1007/s00706-020-02733-z

  日期：2021.1

  form of organic perchlorates have been obtained by the interaction of 1,3-benzo(naphtho)dioxin-4(1)-ones with the Vilsmeier-Haack reagent at 110 °C for 5 h. The rearrangement has occurred as an electrophilic triggered recyclization due to the geminal arrangement of oxygen atoms in the six-membered ring as well as the presence of a lactone group in the structure of the starting 1,3-benzo(naphtho)dioxin-4(1)-ones

  通过在110°C下将1,3-苯并（萘）二恶英-4（1）-1与Vilsmeier-Haack试剂相互作用5 h，获得了有机高氯酸盐形式的黄嘌呤和苯并氧杂蒽的多官能衍生物。由于六元环中氧原子的双键排列以及起始的1,3-苯并（萘）二恶英-4（内酯基团）中内酯基团的存在，重排反应作为亲电触发的再循环发生。 1）-个。 图形摘要
• Triphenyl Ether Amide as a Probe for Electrochemical and Optical Sensing of Copper, Cyanide and Arginine
  作者：Shivali Gupta、Susheel K Mittal、Manmohan Chhibber

  DOI：10.1149/1945-7111/abcbb0

  日期：2020.12.1

  lower detection limit of 4 μM. Host-guest interactions between TPEAM and Cu2+ ions and intramolecular charge transfer interactions (ICT) for CN− ions are proposed as possible mechanisms for the sensing of respective ions. Cyanide detection followed a non-sequential mechanism. The application of TPEAM as a probe for Cu2+ ions has also been validated on food samples and the results are compared with atomic

  新型三苯醚酰胺（TPEAM）衍生物已经合成并开发为探针，用于在其他氨基酸存在下对铜，氰化物离子和精氨酸进行电化学和光学传感。离子载体是选择性关于各种阳离子和阴离子之间的铜和氰化物离子，以检测限为40 nM的和0.4 μ分别男，。TPEAM-Cu（II）络合物的微分脉冲伏安图中的尖锐的阳极和阴极峰表明配体分子具有良好的络合趋势，并且通过分光荧光法和1 H NMR滴定证实了这一点。TPEAM-Cu 2+络合物在水介质中进一步检测到精氨酸（一种半必需氨基酸），最低检测限为4μTPEAM和Cu之间M.主客体相互作用2+离子和CN分子内电荷转移的相互作用（ICT）-离子被提出作为用于各个离子的感测机制。氰化物检测遵循非顺序机制。TPEAM作为Cu 2+离子探针的应用也已在食品样品上得到验证，并将结果与​​原子吸收光谱法进行了比较。
• Method for producing naphthalene carboxylic acid amide compound
  申请人：Wakamori Hiroyuki

  公开号：US20080045720A1

  公开（公告）日：2008-02-21

  The present invention provides a method for producing a naphthalenecarboxylic acid amide compound represented by formula [1] comprising, reacting a naphthalenecarboxylic acid halide compound represented by formula [2] with ammonium acetate in a solvent having an ether bond. According to the method of the present invention, a naphthalene carboxylic acid amide compound can be obtained at high yield and at low cost.

  本发明提供了一种制备萘甲酸酰胺化合物（由式[1]表示）的方法，包括将由式[2]表示的萘甲酸卤化物与醋酸铵在具有醚键的溶剂中反应。根据本发明的方法，可以以高收率和低成本获得萘甲酸酰胺化合物。
• Searching new structural scaffolds for BRAF inhibitors. An integrative study using theoretical and experimental techniques
  作者：Ludmila E. Campos、Francisco M. Garibotto、Emilio Angelina、Jiri Kos、Tihomir Tomašič、Nace Zidar、Danijel Kikelj、Tomas Gonec、Pavlina Marvanova、Petr Mokry、Josef Jampilek、Sergio E. Alvarez、Ricardo D. Enriz

  DOI：10.1016/j.bioorg.2019.103125

  日期：2019.10

  The identification of the V600E activating mutation in the protein kinase BRAF in around 50% of melanoma patients has driven the development of highly potent small inhibitors (BRAFi) of the mutated protein. To date, Dabrafenib and Vemurafenib, two specific BRAFi, have been clinically approved for the treatment of metastatic melanoma. Unfortunately, after the initial response, tumors become resistant and patients develop a progressive and lethal disease, making imperative the development of new therapeutic options. The main objective of this work was to find new BRAF inhibitors with different structural scaffolds than those of the known inhibitors. Our study was carried out in different stages; in the first step we performed a virtual screening that allowed us to identify potential new inhibitors. In the second step, we synthesized and tested the inhibitory activity of the novel compounds founded. Finally, we conducted a molecular modelling study that allowed us to understand interactions at the molecular level that stabilize the formation of the different molecular complexes.Our theoretical and experimental study allowed the identification of four new structural scaffolds, which could be used as starting structures for the design and development of new inhibitors of BRAF. Our experimental data indicate that the most active compounds reduced significantly ERK1/2 phosphorylation, a measure of BRAF inhibition, and cell viability. Thus, from our theoretical and experimental results, we propose new substituted hydroxynaphthalenecarboxamides, N-(hetero)aryl-piperazinylhydroxyalkylphenylcarbamates, substituted piperazinylethanols and substituted piperazinylpropandiols as initial structures for the development of new inhibitors for BRAF. Moreover, by performing QTAIM analysis, we are able to describe in detail the molecular interactions that stabilize the different Ligand-Receptor complexes. Such analysis indicates which portion of the different molecules must be changed in order to obtain an increase in the binding affinity of these new ligands.