4-甲氧基-N-(3,5-二甲氧基苯基)苯甲酰胺 | 134029-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲氧基-N-(3,5-二甲氧基苯基)苯甲酰胺
• 英文名称: N-(3,5-dimethoxyphenyl)-4'-methoxybenzamide
• 英文别名: 4-methoxy-benzoic acid-(3,5-dimethoxy-anilide)；4-Methoxy-benzoesaeure-(3,5-dimethoxy-anilid)；N-(3,5-dimethoxyphenyl)-4-methoxybenzamide
• CAS: 134029-84-8
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: FTFBZINSKZOBTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-甲氧基-N-(3,5-二甲氧基苯基)苯甲酰胺 在 四氯化锡 、 copper(II) oxide 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 34.0h， 生成 4-[5,7-Dimethoxy-2-(4-methoxyphenyl)-4-oxoquinolin-1-yl]sulfonylbenzonitrile
  参考文献：
  名称：

  Novel vitexin-inspired scaffold against leukemia

  摘要：

  Acute lymphoblastic leukemia (ALL) is the most common type of leukemia in children. Up to a quarter of ALL patients relapse and face poor prognosis. To identify new compound leads, we conducted a phenotypic screen using terrestrial natural product (NP) fractions against immortalized ALL cellular models.We identified vitexin, a flavonoid, as a promising hit with biological activity (EC50 = 30 mu M) in pre-B cell ALL models with no toxicity against normal human tissue (BJ cells) at the tested concentrations. To develop more potent compounds against ALL and elucidate its potential mode of action, a vitexin-inspired compound library was synthesized. Thus, we developed an improved and scalable protocol for the direct synthesis of 4-quinolone core heterocycles containing an N-sulfonamide using a one-pot condensation reaction protocol. The newly generated compounds represent a novel molecular scaffold against ALL as exemplified by compounds 13 and 15, which demonstrated EC50 values in the low micromolar range (0.3-10 mu M) with little to no toxicity in normal cellular models. Computational studies support the hypothesis that these compounds are potential CDK inhibitors. The compounds induced apoptosis, caused cell arrest at G0/G1 and G2/M, and induced ROS in cancer cells. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.01.004
• 作为产物：
  描述：

  5-氨基-1,3-苯二酚 在 吡啶 、 sodium hydroxide 、 丙酮 作用下， 生成 4-甲氧基-N-(3,5-二甲氧基苯基)苯甲酰胺
  参考文献：
  名称：

  Sorm; Novotny, Chemicke Listy, 1954, vol. 49, p. 901,907

  摘要：

  DOI：

文献信息

• Synthesis of heterocycle-based analogs of resveratrol and their antitumor and vasorelaxing properties
  作者：Simone Bertini、Vincenzo Calderone、Isabella Carboni、Roberta Maffei、Alma Martelli、Adriano Martinelli、Filippo Minutolo、Mehdi Rajabi、Lara Testai、Tiziano Tuccinardi、Riccardo Ghidoni、Marco Macchia

  DOI：10.1016/j.bmc.2010.07.059

  日期：2010.9

  New resveratrol (RES) analogs were developed by replacing the aromatic ‘core’ of our initial naphthalene-based RES analogs with pseudo-heterocyclic (salicylaldoxime) or heterocyclic (benzofuran, quinoline, and benzothiazole) scaffolds. The resulting analogs were tested for their antiproliferative and vasorelaxing effect, two typical properties shown by RES. Some of the new compounds confirmed strong

  通过用假杂环（水杨醛肟）或杂环（苯并呋喃，喹啉和苯并噻唑）支架取代我们最初的萘基RES类似物的芳族“核心”，开发了新的白藜芦醇（RES）类似物。测试了所得类似物的抗增殖和血管松弛作用，这是RES显示的两个典型特性。一些新化合物证实了很强的抗增殖活性，可与以前以最具活性的萘基类似物发现的抗坏血酸相媲美。特别地，3-（3,5-二羟基苯基）-7-羟基喹啉表现出最有效的抗增殖作用（IC 50  = 17.4μM）。在血管测定中，最高效力（pIC 50  = 4.92）和功效（E max 用2-（3，5-二羟基苯基）-6-羟基苯并噻唑获得＝（88.2％）。这些化合物的构象分析表明，对MDA-MB-231癌细胞的抗增殖活性可能与活性最高的化合物的共同空间分布有关，尤其是与三个酚基的空间排列有关。此外，血管松弛性质与通过静电分子电势（ESP）测得的电子性质具有良好的相关性。
• Alkoxy- and amidocarbonylation of functionalised aryl and heteroaryl halides catalysed by a Bedford palladacycle and dppf: a comparison with the primary Pd(ii) precursors (PhCN)2PdCl2 and Pd(OAc)2
  作者：Ian J. S. Fairlamb、Stephanie Grant、Peter McCormack、John Whittall

  DOI：10.1039/b615874a

  日期：——

  The versatility of a Bedford-type palladacycle 1, namely [Pd(µ-Cl)κ2-P,C-P(OC6H2-2,4-tBu2)(OC6H3-2,4-tBu2)2}}2], as a primary Pd source, in combination with the ligand bis-1,1′-(diphenylphosphino)ferrocene (dppf) has been established in carbonylation reactions of aryl and heteroaryl bromides with methanol, piperidine and related nucleophiles. Palladacycle 1 has been compared with other primary Pd sources, e.g. (PhCN)2PdCl2 and Pd(OAc)2. The efficacy of the carbonylation processes appear to be linked to the [Pd] concentration, substrate : catalyst ratio, CO pressure and reaction temperature. In amidocarbonylation, double carbonylation is observed for certain organohalides. In the case of 2,5-dibromopyridine, regioselective amination (Hartwig–Buchwald type) also occurs as a side-reaction.

  一种Bedford型钯环化合物1，即[Pd(µ-Cl)κ2-P,C-P(OC6H2-2,4-tBu2)(OC6H3-2,4-tBu2)2}}2]，作为主要的钯源，其多功能性已在与醇、哌啶及相关亲核试剂的芳基和杂芳基溴化物的羰基化反应中得到证实。钯环化合物1已与其他主要的钯源进行比较，例如(PhCN)2PdCl2和Pd(OAc)2。羰基化过程的有效性似乎与[钯]浓度、底物与催化剂的比例、一氧化碳压力和反应温度有关。在胺羰基化过程中，某些有机卤化物观察到了双羰基化现象。在2,5-二溴吡啶的情况下，还发生了区域选择性氨基化（Hartwig–Buchwald型）的副反应。
• BENZAMIDE DERIVATIVES AND THEIR USE FOR TREATING CNS DISORDERS
  申请人：Galley Guido

  公开号：US20090036420A1

  公开（公告）日：2009-02-05

  The present invention relates to methods of treating CNS disorders with a compound of formula I wherein X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are as defined in the specification and pharmaceutically acceptable acid addition salts thereof.

  本发明涉及使用式I中的化合物治疗中枢神经系统疾病的方法，其中X、R1、R2、R3、R4、R5、R6、R7和R8如说明书中所定义，并且包括药学上可接受的酸盐。
• Synthesis and evaluation of stilbene and dihydrostilbene derivatives as potential anticancer agents that inhibit tubulin polymerization
  作者：Mark Cushman、Dhanapalan Nagarathnam、D. Gopal、Asit K. Chakraborti、Chii M. Lin、Ernest Hamel

  DOI：10.1021/jm00112a036

  日期：1991.8

  An array of cis-, trans-, and dihydrostilbenes and some N-arylbenzylamines were synthesized and evaluated for their cytotoxicity in the five cancer cell cultures A-549 lung carcinoma, MCF-7 breast carcinoma, HT-29 colon adenocarcinoma, SKMEL-5 melanoma, and MLM melanoma. Several cis-stilbenes, structurally similar to combretastatins, were highly cytotoxic in all five cell lines and these were also found to be active as inhibitors of tubulin polymerization. The most active compounds also inhibited the binding of colchicine to tubulin. The most potent of the new compounds, both as a tubulin polymerization inhibitor and as a cytotoxic agent, was (Z)-1-(4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)ethene (5a). This substance was almost as potent as combretastatin A-4 (1a), the most active of the combretastatins, as a tubulin polymerization inhibitor. Compound 5a was found to be approximately 140 times more cytotoxic against HT-29 colon adenocarcinoma cells and about 10 times more cytotoxic against MCF-7 breast carcinoma cells than combretastatin A-4. However, 5a was found to be about 20 times less cytotoxic against A-549 lung carcinoma cells, 30 times less cytotoxic against SKMEL-5 melanoma cells, and 7 times less cytotoxic against MLM melanoma cells than combretastatin A-4. The relative potencies 5a > 8a > 6a for the cis, dihydro, and trans compounds, respectively, as inhibitors of tubulin polymerization are in agreement with the relative potencies previously observed for combretastatin A-4 (1a), dihydrocombretastatin A-4 (1c), and trans-combretastatin A-4 (1b). The relative potencies 5a > 8a > 6a were also reflected in the results of the cytotoxicity assays. Structure-activity relationships of this group of compounds are also discussed.
• Zur Kenntnis methoxylierter Phenylchinolone bzw. 2-Phenyl-4-oxy-chinoline
  作者：Reinhard Seka、Walter Fuchs

  DOI：10.1007/bf01522109

  日期：1931.2