4-nitro-1-nathphoyl chloride | 87700-66-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-nitro-1-nathphoyl chloride
• 英文别名: 4-nitro-1-naphthoyl-chloride；4-Nitro-naphthoesaeure-(1)-chlorid；4-Nitronaphthalene-1-carbonyl chloride
• CAS: 87700-66-1
• 化学式: C₁₁H₆ClNO₃
• 分子量: 235.627
• InChiKey: MJTVOOXYSIKJFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-nitro-1-nathphoyl chloride 在 盐酸 、 三氯化铝 、 镍 、 肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (4-Iodo-naphthalen-1-yl)-[1-(1-methyl-piperidin-2-ylmethyl)-1H-indol-3-yl]-methanone
  参考文献：
  名称：

  Potent Cannabinergic Indole Analogues as Radioiodinatable Brain Imaging Agents for the CB1 Cannabinoid Receptor

  摘要：

  A series of novel aminoalkylindoles was synthesized in an effort to develop compounds that are potent agonists at the CB1 cannabinoid receptor and that are also easily labeled with radioisotopes of iodine for biochemical and imaging studies. 2-iodophenyl-[1-(l-methylpiperidin2-ylmethyl)]-1H-indol-3-yllmethanone (8, AM2233) had a very high affinity for the rat CB1 receptor, with most of the affinity residing with the (R)-enantiomer. Radioiodinated 8, (R)-8, and (S)-8 were prepared by radioiododestannylation of the tributyltin analogues in high yields, radiochemical purities, and specific radioactivities. In a mouse hippocampal membrane preparation with [I-131](R)-8 as radioligand, racemic 8 exhibited a K-i value of 0.2 nM compared with 1.6 nM for WIN55212-2. In autoradiographic experiments with mouse brain sections, the distribution of radioiodinated 8 was consistent with that of brain CB1 receptors. Again, very little specific binding was seen with the (S)-enantiomer [I-131](S)-8 and none occurred with the (R)-enantiomer [I-131] (R)-8 in sections from CB1 receptor knockout mice. Radioiodinated 8 thus appears to be a suitable radioligand for studies of CB1 cannabinoid receptors.

  DOI：

  10.1021/jm050135l
• 作为产物：
  描述：

  4-硝基-1,8-萘醛酸酐 在 sodium hydroxide 、 氯化亚砜 作用下， 反应 99.0h， 生成 4-nitro-1-nathphoyl chloride
  参考文献：
  名称：

  Potent Cannabinergic Indole Analogues as Radioiodinatable Brain Imaging Agents for the CB1 Cannabinoid Receptor

  摘要：

  A series of novel aminoalkylindoles was synthesized in an effort to develop compounds that are potent agonists at the CB1 cannabinoid receptor and that are also easily labeled with radioisotopes of iodine for biochemical and imaging studies. 2-iodophenyl-[1-(l-methylpiperidin2-ylmethyl)]-1H-indol-3-yllmethanone (8, AM2233) had a very high affinity for the rat CB1 receptor, with most of the affinity residing with the (R)-enantiomer. Radioiodinated 8, (R)-8, and (S)-8 were prepared by radioiododestannylation of the tributyltin analogues in high yields, radiochemical purities, and specific radioactivities. In a mouse hippocampal membrane preparation with [I-131](R)-8 as radioligand, racemic 8 exhibited a K-i value of 0.2 nM compared with 1.6 nM for WIN55212-2. In autoradiographic experiments with mouse brain sections, the distribution of radioiodinated 8 was consistent with that of brain CB1 receptors. Again, very little specific binding was seen with the (S)-enantiomer [I-131](S)-8 and none occurred with the (R)-enantiomer [I-131] (R)-8 in sections from CB1 receptor knockout mice. Radioiodinated 8 thus appears to be a suitable radioligand for studies of CB1 cannabinoid receptors.

  DOI：

  10.1021/jm050135l

文献信息

• Receptor Selective Cannabimimetic Aminoalkylindoles
  申请人：Makriyannis Alexandros

  公开号：US20070243134A1

  公开（公告）日：2007-10-18

  Disclosed are cannabimimetic aminoalkylindole compounds and methods for their manufacture. The disclosed compounds are surprisingly potent and selective cannabinoids. The disclosed compounds may include radioactive atoms. Also disclosed are methods of using the disclosed compounds, including use of the disclosed compounds to stimulate a cannabinoid receptor, to provide a physiological effect in an animal or individual, to treat a condition in an animal or individual and for use in radioimaging.

  本发明涉及大麻类氨基烷基吲哚化合物及其制备方法。所述化合物具有惊人的强效和选择性大麻素。所述化合物可能包括放射性原子。本发明还涉及使用所述化合物的方法，包括使用所述化合物刺激大麻素受体，在动物或个体中产生生理效应，治疗动物或个体的疾病以及用于放射性成像。
• Alkylaminoalkyl Esters of Aminonaphthoic Acids as Local Anesthetics
  作者：F. F. Blicke、H. C. Parke

  DOI：10.1021/ja01874a054

  日期：1939.5
• Sergiewskaja; Neswad'ba, Zhurnal Obshchei Khimii, 1938, vol. 8, p. 924,928
  作者：Sergiewskaja、Neswad'ba

  DOI：——

  日期：——
• Conformational studies of tertiary oligo-m-benzanilides and oligo-p-benzanilides in solution
  作者：Laurent Chabaud、Jonathan Clayden、Madeleine Helliwell、Abigail Page、James Raftery、Lluís Vallverdú

  DOI：10.1016/j.tet.2010.06.037

  日期：2010.8

  A series of oligo-m- and p-benzanilides were made and their conformations in solution were studied by NMR. In most cases, conformational mixtures were observed as soon as three or more monomers were incorporated into the oligomer. Some crystal structures were obtained, which indicated that helical conformations were adopted in the solid state. (C) 2010 Elsevier Ltd. All rights reserved.
• Analogues of the Potent Nonpolyglutamatable Antifolate <i>N</i>^α-(4-Amino-4-deoxypteroyl)-<i>N</i>^δ-hemiphthaloyl-<scp>l</scp>-ornithine (PT523) with Modifications in the Side Chain, <i>p</i>-Aminobenzoyl Moiety, or 9,10-Bridge:  Synthesis and in Vitro Antitumor Activity
  作者：Andre Rosowsky、Joel E. Wright、Chitra M. Vaidya、Ronald A. Forsch、Henry Bader

  DOI：10.1021/jm990630f

  日期：2000.4.1

  Seven N-alpha-(4-amino-4-deoxypteroyl)-N-sigma-hemiphtha (2, PT523) analogues were synthesized by modifications of the literature synthesis of the corresponding AMT (1) analogues and were tested as inhibitors of tumor cell growth. in growth assays against cultured CCRF-CEM human leukemic cells exposed to drug for 72 h, the IC50 values of analogues in which N-10 was replaced by CH2 and CHMe were found to be 0.55 +/- 0.07 and 0.63 +/- 0.08 nM, and thus these analogues are more potent than 1 (IC50 = 4.4 +/- 1.0 nM) or 2 (IC50 = 1.5 +/-: 0.39 nM). The 10-ethyl-10-deaza analogue of 2 (IC50 = 1.2 +/- 0.25 nM) was not statistically different from 2 but was more potent than edatrexate, the 10-ethyl-10-deaza analogue of 1, which had an IC50 of 3.3 +/- 0.36 nM. In contrast, the analogue of 2 with both an ethyl and a CO2Me group at the 10-position had an IC50 of 54 +/- 4.9 nM, showing this modification to be unfavorable. The 4-amino-1-naphthoic acid analogue of 2 had an IC50 Of 1.2 +/- 0.22 nM, indicating that replacement of the p-aminobenzoic acid (pABA) moiety does not diminish cytotoxicity. The analogues in which the (CH2)(3) Side chain was replaced by slightly longer CH2SCH2 and (CH2)(2)-SCH2 groups gave IC50 values of 4.4 +/- 1.1 and 5.0 +/- 0.56 nM and thus were somewhat less potent than the parent molecule. However the analogues in which the aromatic COOH group was at the meta and para positions of the phthaloyl ring had IC50 values of 7.5 +/- 0.47 and 55 +/- 0.07 nM, confirming the low potency we had previously observed with these compounds against other cell lines. Overall, the results in this study support the conclusion that, while the position of the phthaloyl COOH group and the length of the amino acid side chain in 2 are important determinants of cytotoxic potency, changes in the pABA region and 9,10-bridge are well-tolerated and can even increase potency.