N-(4-bromophenyl)-3-hydroxynaphthalene-2-carboxamide | 50729-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(4-bromophenyl)-3-hydroxynaphthalene-2-carboxamide
• 英文别名: 3-hydroxy-N-(4-bromophenyl)-2-naphthamide；3-hydroxy-[2]naphthoic acid-(4-bromo-anilide)；3-Hydroxy-[2]naphthoesaeure-(4-brom-anilid)；N-(4-bromophenyl)-3-hydroxy-2-naphthamide
• CAS: 50729-40-3
• 化学式: C₁₇H₁₂BrNO₂
• 分子量: 342.192
• InChiKey: HBCJKVALTGCACO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-二氯-1,4-萘醌 、 N-(4-bromophenyl)-3-hydroxynaphthalene-2-carboxamide 在 吡啶 、 甲苯 作用下， 生成 8,13-dioxo-8,13-dihydro-dinaphtho[2,1-b;2',3'-d]furan-6-carboxylic acid-(4-bromo-anilide)
  参考文献：
  名称：

  Dikshit et al., Proceedings - Indian Academy of Sciences, Section A, 1953, # 37, p. 92,94

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基-3-萘甲酸 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 N-(4-bromophenyl)-3-hydroxynaphthalene-2-carboxamide
  参考文献：
  名称：

  Structure–activity relationship studies of naphthol AS-E and its derivatives as anticancer agents by inhibiting CREB-mediated gene transcription

  摘要：

  CREB (cyclic AMP-response element binding protein) is a downstream transcription factor of a multitude of signaling pathways emanating from receptor tyrosine kinases or G-protein coupled receptors. CREB is not activated until it is phosphorylated at Ser133 and its subsequent binding to CREB-binding protein (CBP) through kinase-inducible domain (KID) in CREB and KID-interacting (KIX) domain in CBP. Tumor tissues from various organs present higher level of expression and activation of CREB. Thus CREB has been proposed as a promising cancer drug target. We previously described naphthol AS-E (1a) as a small molecule inhibitor of CREB-mediated gene transcription in living cells. Here we report the structure-activity relationship (SAR) studies of la by modifying the appendant phenyl ring. All the compounds were evaluated for in vitro inhibition of KIX-KID interaction, cellular inhibition of CREB-mediated gene transcription and inhibition of proliferation of four cancer cell lines (A549, MCF-7, MDA-MB-231 and MDA-MB-468). SAR indicated that a small and electron-withdrawing group was preferred at the para-position for KIX-KID interaction inhibition. Compound la was selected for further biological characterization and it was found that la down-regulated the expression of endogenous CREB target genes. Expression of a constitutively active CREB mutant, VP16-CREB in MCF-7 cells rendered the cells resistant to la, suggesting that CREB was critical in mediating its anticancer activity. Furthermore, la was not toxic to normal human cells. Collectively, these data support that la represents a structural template for further development into potential cancer therapeutics with a novel mechanism of action. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.056

文献信息

• 3-Hydroxynaphthalene-2-carboxanilides and their antitrypanosomal activity
  作者：Jiri Kos、Iva Kapustikova、Carol Clements、Alexander I. Gray、Josef Jampilek

  DOI：10.1007/s00706-017-2099-1

  日期：2018.5

  and acid–base dissociation constants of the compounds as well as with the calculated electronic properties of individual anilide substituents expressed as Hammett’s σ parameters. The substitution in the meta- or para-position of anilide of derivatives with higher lipophilicity by an electron-withdrawing moiety is favourable for higher activity. The optimum thermodynamic pK Ta value was found to be

  摘要筛选了一系列环取代的3-羟基萘-2-甲酰苯胺对布鲁氏锥虫的野生型S427（血流形式）的体外活性。3-羟基-N-（3-三氟甲基苯基）-和3-羟基-N-（4-三氟甲基苯基）萘-2-甲酰胺显示出最高的生物活性（分别为MIC ＝ 1.56和2.08μmol/ dm 3）。抗锥体虫活性与用表达为哈米特个别苯胺的取代基的所计算出的电子性质的化合物的以及试验确定亲脂性和酸-碱的解离常数相关σ参数。在meta或para中的替换具有较高亲脂性的衍生物的苯胺通过吸电子部分的位置有利于较高的活性。发现最佳热力学p K T a值为约。7.5。讨论了所有化合物的结构活性关系。 图形概要
• Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides
  作者：Jiri Kos、Iveta Zadrazilova、Matus Pesko、Stanislava Keltosova、Jan Tengler、Tomas Gonec、Pavel Bobal、Tereza Kauerova、Michal Oravec、Peter Kollar、Alois Cizek、Katarina Kralova、Josef Jampilek

  DOI：10.3390/molecules18077977

  日期：——

  In this study, a series of twenty-two ring-substituted 3-hydroxy-N-phenylnaphthalene-2-carboxanilides were prepared and characterized. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four Staphylococcus strains

  在本研究中，制备并表征了一系列 22 个环取代的 3-羟基-N-苯基萘-2-甲酰苯胺。测试了这些化合物与抑制菠菜 (Spinacia oleracea L.) 叶绿体中光合电子传递 (PET) 相关的活性。还针对四种葡萄球菌菌株和两种分枝杆菌物种对合成化合物进行了初步体外筛选。3-Hydroxy-N-(2-甲氧基苯基)naphthalene-2-carboxamide 对金黄色葡萄球菌和耐甲氧西林菌株显示出高生物活性 (MIC = 55.0 µmol/L)。N-(2-氟苯基)-3-羟基萘-2-甲酰胺对海藻的活性(MIC = 28.4 µmol/L)高于标准异烟肼和3-羟基-N-(4-硝基苯基)萘-2-甲酰胺表现出更高的活性（MIC = 13. 0 µmol/L) 对抗 M. kansasii 比标准异烟肼。使用人单核细胞白血病 THP-1 细胞系进行有效抗微生物化合物的细胞毒性测定。以活性
• Process for producing azo pigments
  申请人：Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo

  公开号：EP0190947A2

  公开（公告）日：1986-08-13

  A process for producing azo pigments which are toned comprises coupling an aromatic diazonium compound with 3-hydroxy-2-naphthoic acid and at least one bis-naphthyl- methane, and optionally, laking the resulting pigment.

  生产调色偶氮颜料的工艺包括：将芳香族重氮化合物与 3-羟基-2-萘酸和至少一种双萘甲烷偶联，然后将得到的颜料浸泡。
• <p>Reversible Small Molecule Inhibitors of MAO A and MAO B with Anilide Motifs</p>
  作者：Jens Hagenow、Stefanie Hagenow、Kathrin Grau、Mohammad Khanfar、Lena Hefke、Ewgenij Proschak、Holger Stark

  DOI：10.2147/dddt.s236586

  日期：——

  Background: Ligands consisting of two aryl moieties connected via a short spacer were shown to be potent inhibitors of monoamine oxidases (MAO) A and B, which are known as suitable targets in treatment of neurological diseases. Based on this general blueprint, we synthesized a series of 66 small aromatic amide derivatives as novel MAO A/B inhibitors.Methods: The compounds were synthesized, purified and structurally confirmed by spectroscopic methods. Fluorimetric enzymological assays were performed to determine MAO A/B inhibition properties. Mode and reversibility of inhibition was determined for the most potent MAO B inhibitor. Docking poses and pharmacophore models were generated to confirm the in vitro results.Results: N-(2,4-Dinitrophenyl)benzo [d] [1,3]dioxole-5-carboxamide (55, ST-2043) was found to be a reversible competitive moderately selective MAO B inhibitor (IC50 = 56 nM, K-i = 6.3 nM), while N-(2,4-dinitrophenyl)benzamide (7, ST-2023) showed higher preference for MAO A (IC50 = 126 nM). Computational analysis confirmed in vitro binding properties, where the anilides examined possessed high surface complementarity to MAO A/B active sites.Conclusion: The small molecule anilides with different substitution patterns were identified as potent MAO A/B inhibitors, which were active in nanomolar concentrations ranges. These small and easily accessible molecules are promising motifs, especially for newly designed multitargeted ligands taking advantage of these fragments.
• Naphthalene carboxamides as inhibitors of human cytomegalovirus DNA polymerase
  作者：Valerie A Vaillancourt、Michele M Cudahy、Sandra A Staley、Roger J Brideau、Steven J Conrad、Mary L Knechtel、Nancee L Oien、Janet L Wieber、Yoshihiko Yagi、Michael W Wathen

  DOI：10.1016/s0960-894x(00)00402-9

  日期：2000.9

  ortho-Hydroxynaphthalene carboxamides have been identified as inhibitors of HCMV DNA polymerase. SAR investigations have demonstrated that both the amide and hydroxy functionalities are required for activity. Substitution on the naphthalene ring has led to inhibitors with submicromolar IC(50)s against HCMV polymerase. These compounds have been found to be >100-fold selective for inhibition of HCMV polymerase versus human alpha polymerase and display antiviral activity in a cell-based plaque reduction assay. (C) 2000 Elsevier Science Ltd. All rights reserved.