4-Brom-1-methoxynaphthalin-2-carbonsaeurechlorid | 152565-77-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-Brom-1-methoxynaphthalin-2-carbonsaeurechlorid
• 英文别名: 1-methoxy-4-bromo-2-naphthoyl chloride；4-bromo-1-methoxy-2-naphthoyl chloride；4-bromo-1-methoxy-[2]naphthoyl chloride；4-Brom-1-methoxy-naphthoesaeure-(2)-chlorid；4-Brom-1-methoxy-[2]naphthoylchlorid；4-bromo-1-methoxynaphthalene-2-carbonyl chloride
• CAS: 152565-77-0
• 化学式: C₁₂H₈BrClO₂
• 分子量: 299.551
• InChiKey: ZXCNADNPEWTQJO-UHFFFAOYSA-N

物化性质

• 熔点：
  114-115 °C
• 沸点：
  417.5±30.0 °C(Predicted)
• 密度：
  1.575±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Brom-1-methoxynaphthalin-2-carbonsaeurechlorid 在 盐酸 、 ammonium acetate 、 copper(I) bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 37.0h， 生成 2-(4-Bromo-1-methoxy-2-naphthalenyl)-1H-pyrrole
  参考文献：
  名称：

  2-（5-溴-2,3-二甲氧基苯基）-5-（氨基甲基）-1H-吡咯类似物的合成及其对多巴胺D2，D3和D4受体的结合亲和力。

  摘要：

  一系列2-（5-溴-2,3-二甲氧基苯基）-5-（氨基甲基）-1H-吡咯类似物的制备及其对多巴胺D（2），D（3）和D（4）受体的亲和力使用体外结合测定法测量。受体结合研究的结果表明，在苯环和碱性氮之间引入吡咯部分会导致多巴胺D（3）受体的选择性显着提高。该系列中最具选择性的化合物是2-（5-溴-2,3-二甲氧基苯基）-5-（2-（3-吡啶基）哌啶基）甲基-1H-吡咯（6p），其具有D（3）受体亲和力为4.3 nM，对D（3）与D（2）受体的选择性是20倍，对D（3）与D（4）受体的选择性是300倍。预计该化合物是用于研究体内多巴胺D（3）受体的功能作用的有用配体。

  DOI：

  10.1016/s0968-0896(02)00341-3
• 作为产物：
  描述：

  1-甲氧基-2-萘甲酸 在 五氯化磷 、 溴 、 溶剂黄146 、 Petroleum ether 、 苯 作用下， 生成 4-Brom-1-methoxynaphthalin-2-carbonsaeurechlorid
  参考文献：
  名称：

  Jadhav; Rao, Journal of the Indian Chemical Society, 1936, vol. 13, p. 645,648

  摘要：

  DOI：

文献信息

• Aryl nitrogen-containing bicyclic compounds and methods of use
  申请人：Patel F. Vinod

  公开号：US20070054916A1

  公开（公告）日：2007-03-08

  The present invention comprises a new class of compounds useful for the prophylaxis and treatment of protein kinase mediated diseases, including inflammation, cancer and related conditions. The compounds have a general Formula I wherein A 1 , A 2 , A 3 , B, R 1 , R 2 , R 3 and R 4 are defined herein. Accordingly, the invention also comprises pharmaceutical compositions comprising the compounds of the invention, methods for the prophylaxis and treatment of kinase mediated diseases using the compounds and compositions of the invention, and intermediates and processes useful for the preparation of compounds of the invention.

  这项发明涉及一类新的化合物，用于预防和治疗蛋白激酶介导的疾病，包括炎症、癌症和相关疾病。这些化合物具有一般的化学式I，其中A1、A2、A3、B、R1、R2、R3和R4在此有定义。因此，该发明还涉及包括该发明的化合物的药物组合物，使用该发明的化合物和组合物预防和治疗激酶介导的疾病的方法，以及用于制备该发明的化合物的中间体和方法。
• Phenyloxazoles and phenylthiazoles as benzamide bioisosteres: synthesis and dopamine receptor binding profiles
  作者：Jürgen Einsiedel、Christoph Thomas、Harald Hübner、Peter Gmeiner

  DOI：10.1016/s0960-894x(00)00405-4

  日期：2000.9

  Conformationally restricted benzamide bioisosteres were investigated when the aminomethylpyrrolidine derivative 4o proved D3 as well as D4 binding properties which were comparable to those of the atypical neuroleptics sulpiride and clozapine, respectively.

  当氨基甲基吡咯烷衍生物4o证明了D3和D4的结合特性分别与非典型的抗精神病药舒必利和氯氮平相当时，研究了构象受限的苯甲酰胺生物异构体。
• HETEROARYL-SUBSTITUTED ALKYNE COMPOUNDS AND METHOD OF USE
  申请人：Chaffee Stuart C.

  公开号：US20100160283A1

  公开（公告）日：2010-06-24

  The present invention comprises a new class of compounds useful for the prophylaxis and treatment of protein kinase mediated diseases, including inflammation, cancer and related conditions. The compounds have a general Formula I wherein A 1 , A 2 , A 3 , A 4 , R 1 and R 2 are defined herein. Accordingly, the invention also comprises pharmaceutical compositions comprising the compounds of the invention, methods for the prophylaxis and treatment of kinase mediated diseases using the compounds and compositions of the invention, and intermediates and processes useful for the preparation of compounds of the invention.

  本发明涉及一类新的化合物，用于预防和治疗蛋白激酶介导的疾病，包括炎症、癌症和相关疾病。该化合物具有一般式I，其中A1、A2、A3、A4、R1和R2的定义如本文所述。因此，本发明还涉及包括本发明化合物的制药组合物，使用本发明化合物和组合物预防和治疗激酶介导的疾病的方法，以及用于制备本发明化合物的中间体和过程。
• Synthesis and Structure−Activity Relationships of Naphthamides as Dopamine D₃ Receptor Ligands
  作者：Yunsheng Huang、Robert R. Luedtke、Rebekah A. Freeman、Li Wu、Robert H. Mach

  DOI：10.1021/jm0100077

  日期：2001.5.1

  A series of naphthamides were synthesized, and the affinities of these compounds were determined for dopamine D-2 and D-3 receptors using radioligand binding techniques. The naphthamide compounds that were prepared include N-(1-alkylpiperidin-4-yl)-4-bromo-1-methoxy-2-naphthamides (1-6), (S)-N-(1-alkylpyrrolidin-3-yl)-4-bromo-1-methoxy-2-naphthamides (7-12), (R)-N-(1-alkylpyrrolidin-3-yl)-4-bromo-1-methoxy-2-naphthamides (13-18), (S)-N-(1-alkyl-2-pyrrolidinylmethyl)-4-bromo-1-methoxy-2-naphthamides (19 -25), (R)-N-(1-alkyl-2-pyrrolidinylmethyl)-4-bromo-1-methoxy-2-naphthamides (26-31), and N-(9-alkyl-9-azabicyclo-[3.3.1]nonan-3 beta -yl)-4- bromo-1-methoxy-2-naphthamides (32, 33). The results of in vitro radioligand binding studies indicated that the majority of the naphthamide analogues bound with high affinity at both the D-2 and D-3 dopamine receptor subtypes and most of the compounds demonstrated some selectivity for the dopamine D-3 dopamine receptor subtype. These results demonstrated that both the structure of the central amine moiety (piperidine, pyrrolidine, and 9-azabicyclo[3.3.1]nonane) ring and the N-(alkyl) substitution on the amine significantly effects the binding affinity at D-2 and D-3 dopamine receptors. The bulkiness of the N-(1-alkyl) substituent was found to (a) have no effect on pharmacologic selectivity, (b) increase the affinity at Ds receptors, or (c) decrease the affinity at D-2 receptors. The most potent analogue in this series was (S)-N-(1-cycloheptylpyrrolidin-3-yl)-4-bromo-1-methoxy-2-naphthamide (10), which had equilibrium dissociation (K-i) values of 1.8 and 0.2 nM for D-2 and D-3 receptors, respectively. The most selective analogue was (R)-N-(1-cycloheptyl-2-pyrrolidinylmethyl)-4-bromo-1-methoxy-2-naphthamide (30), which had K-i values of 62.8 and 2.4 nM for D-2 and D-3 receptors, respectively. Radioligand binding results for sigma receptors indicated that the structure of the amine moiety and the N-(l-alkyl) substitutions also significantly influence the affinity and selectivity of these compounds at the sigma (1) and sigma (2) sigma receptor subtypes. The two naphthamides containing a 9-azabicyclo[3.3.1]nonan-3 beta -yl central ring were found to be selective for sigma (2) receptors.
• Mach, Robert H.; Hammond, Philip S.; Huang, Yunsheng, Medicinal Chemistry Research, 1999, vol. 9, # 6, p. 355 - 373
  作者：Mach, Robert H.、Hammond, Philip S.、Huang, Yunsheng、Yang, Biao、Xu, Yueping、Cheney, Jason T.、Freeman, Rebekah、Luedtke, Robert R.

  DOI：——

  日期：——