N-(4-氟苯基)-4-硝基苯甲酰胺 | 347-81-9

• 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: N-(4-氟苯基)-4-硝基苯甲酰胺
• 英文名称: N-(4-fluorophenyl)-4-nitrobenzamide
• CAS: 347-81-9
• 化学式: C₁₃H₉FN₂O₃
• mdl: MFCD00171570
• 分子量: 260.224
• InChiKey: IKNWALBEQFNHIW-UHFFFAOYSA-N

物化性质

• 保留指数：
  2362

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(4-氟苯基)-4-硝基苯甲酰胺 在 劳森试剂 、 六甲基磷酰三胺 、 sodium hydroxide 、 一氯化碘 、 溶剂黄146 、 tin(ll) chloride 、 potassium hexacyanoferrate(III) 作用下， 以 乙醇 为溶剂， 反应 23.0h， 生成 2-(4-amino-3-iodophenyl)-6-fluorobenzothiazole
  参考文献：
  名称：

  Antitumor Benzothiazoles. 14. Synthesis and in Vitro Biological Properties of Fluorinated 2-(4-Aminophenyl)benzothiazoles

  摘要：

  Synthetic routes to a series of mono- and difluorinated 2-(4-amino-3-substituted-phenyl)benzothiazoles have been devised. Whereas mixtures of regioisomeric 5- and 7-fluorobenzothiazoles were formed from the established Jacobsen cyclization of precursor 3-fluorothiobenzanilides, two modifications to this general process have allowed the synthesis of pure samples of these target compounds. Fluorinated 2-(4-aminophenyl)benzothiazoles were potently cytotoxic (GI(50) < 1 nM) in vitro in sensitive human breast MCF-7 (ER+) and MDA 468 (ER-) cell lines but inactive (GI(50) > 10 muM) against PC 3 prostate, nonmalignant HBL 100 breast, and HCT 116 colon cells. The biphasic dose-response relationship characteristically shown by the benzothiazole series against sensitive cell lines was exhibited by the 4- and 6-fluorobenzothiazoles (10b,d) but not by the 5- and 7-fluoro-benzothiazoles (10h,i). The most potent broad spectrum agent in the NCI cell panel was 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (10h) which, unlike the g-fluoro isomer (10d), produces no exportable metabolites in the presence of sensitive MCF-7 cells. Induction of cytochrome P450 CYP1A1, a crucial event in determining the antitumor specificity of this series of benzothiazoles, was not compromised. 10h is currently the focus of pharmaceutical and preclinical development.

  DOI：

  10.1021/jm001104n
• 作为产物：
  描述：

  4-硝基苯甲酰替苯胺 在 二(叔丁基羰基氧基)碘苯 、 氟化氢吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以50%的产率得到N-(4-氟苯基)-4-硝基苯甲酰胺
  参考文献：
  名称：

  Hypervalent Iodine Mediated para-Selective Fluorination of Anilides

  摘要：

  A metal-free method for the direct regioselective fluorination of anilides has been developed. In the presence of bis(tert-butylcarbonyloxy)iodobenzene (PhI(OPiv)(2)) and hydrogen fluoride-pyridine, the para-fluorination products of anilides were obtained in moderate to good yields. Because of its operational safety and the use of readily available reagents, this new procedure provides facile access to a variety of para-fluorinated anilides.

  DOI：

  10.1021/jo302099d

文献信息

• Applicability of aluminum amalgam to the reduction of arylnitro groups
  作者：Paige J. Monsen、Frederick A. Luzzio

  DOI：10.1016/j.tetlet.2020.152575

  日期：2020.11

  compounds with various functionality were treated with freshly-prepared aluminum amalgam in THF/water solution and resulted in the corresponding arylamines. The Al(Hg)-mediated reductions are relatively rapid with consumption of the amalgam and disappearance of starting material occurring over 20–30 min. The workup of the reductions involves only removal of the insoluble by-products by filtration followed

  一系列具有不同官能度的芳基硝基化合物用新制备的铝汞齐在 THF/水溶液中处理，得到相应的芳胺。随着汞合金的消耗和起始材料的消失，Al(Hg) 介导的还原速度相对较快，超过 20-30 分钟。还原的处理只涉及通过过滤和浓缩去除不溶性副产物。只有在某些情况下才需要色谱法来确保纯产品。所需的芳胺以 25–100 mg 的量提供，在某些情况下，无需进一步纯化即可用于下一步反应。碳水化合物或核苷的 4-硝基苄基衍生物的还原在提供相应的 4-氨基苄基产物方面具有选择性。
• Design, synthesis and biological evaluation of novel 2-phenyl pyrimidine derivatives as potent Bruton's tyrosine kinase (BTK) inhibitors
  作者：Xinyu Li、Binyu Shi、Yu Teng、Yu Cheng、Huizhu Yang、Jiurong Li、Lianjian Wang、Siying He、Qidong You、Hua Xiang

  DOI：10.1039/c8md00413g

  日期：——

  with the positive control ibrutinib. The mechanism investigation demonstrated that 11g could inhibit the phosphorylation of BTK and its downstream substrate phospholipase γ2 (PLCγ2). All these results showed that 11g was a promising lead compound that merited further optimization as a novel class of BTK inhibitor for the treatment of B-cell lymphoblastic leukemia.

  BTK是治疗B细胞恶性肿瘤和自身免疫性疾病的有效靶标。在这项工作中，制备了一系列的2-苯基嘧啶衍生物，并确定了它们对B细胞白血病细胞以及BTK酶的初步体外活性。结果表明，化合物11g对BTK表现出最佳的抑制活性，在100 nM时抑制率达82.76％，对三种B细胞白血病系（IC50分别对HL60的抑制率分别为3.66μM，6.98μM和5.39μM）。 ，拉吉（Raji）和拉莫斯（Ramos））。此外，流式细胞仪分析结果表明11g以剂量和时间依赖性方式抑制Raji细胞的增殖，并在G0 / G1期阻断Ramos细胞，这与阳性对照依鲁替尼一致。机理研究表明，11g可以抑制BTK及其下游底物磷脂酶γ2（PLCγ2）的磷酸化。所有这些结果表明，11g是有前途的先导化合物，值得进一步优化，作为治疗B细胞淋巴细胞白血病的新型BTK抑制剂。
• Novel series of benzo[d]thiazolyl substituted-2-quinolone hybrids: Design, synthesis, biological evaluation and in-silico insights
  作者：Girish Bolakatti、Mahesh Palkar、Manjunatha Katagi、Girish Hampannavar、Rajshekhar V. Karpoormath、Shilpa Ninganagouda、Arvind Badiger

  DOI：10.1016/j.molstruc.2020.129413

  日期：2021.3

  Abstract A novel series of 3-(2-(4-(substituted-benzo[d]thiazol-2-yl)phenylamino)acetyl)-4‑hydroxy-1-methyl/phenyl quinolin-2(1H)-one (7a-f and 8a-f) were synthesized. Reaction of appropriately substituted-2-(4-amino phenyl)benzo[d]thiazole (4a-f) with 3-(2-bromoacetyl)-4‑hydroxy-1-methyl/phenyl quinolin-2(1H)-one (5/6) in the presence of glacial acetic acid resulted in desired compounds. Structures

  摘要 3-(2-(4-(取代-苯并[d]噻唑-2-基)苯基氨基)乙酰基)-4-羟基-1-甲基/苯基喹啉-2(1H)-酮(7a -f 和 8a-f) 合成。适当取代的 2-(4-氨基苯基)苯并[d]噻唑 (4a-f) 与 3-(2-溴乙酰基)-4-羟基-1-甲基/苯基喹啉-2(1H)-one 的反应 ( 5/6) 在冰醋酸的存在下产生所需的化合物。合成化合物的结构基于它们的光谱（IR、1H NMR、13C NMR和MS）和元素分析来表征。细胞毒性筛选研究表明，MCF-7 和 WRL68 癌细胞对所有测试化合物均敏感。在 12 种新型杂交体中，化合物 8f 显示出最显着的抗癌活性。进行对接研究以了解标题化合物在目标酶（EGFR 酪氨酸激酶，1M17）活性位点的结合模式。化合物 8f 和 7f 显示出针对 1M17 的显着且保守的结合相互作用。此外，化合物 7e、7f、8e 和 8f 表现出有趣
• Identification of new pyrrolo[2,3-d]pyrimidines as potent VEGFR-2 tyrosine kinase inhibitors: Design, synthesis, biological evaluation and molecular modeling
  作者：Mai Adel、Rabah A.T. Serya、Deena S. Lasheen、Khaled A.M. Abouzid

  DOI：10.1016/j.bioorg.2018.09.001

  日期：2018.12

  ability to inhibit VEGFR-2 kinase enzyme in vitro. All the tested compounds demonstrated highly potent dose-related VEGFR-2 inhibition with IC50 values in nanomolar range. Among these compounds, pyrrolo[2,3-d]pyrimidine derivatives carrying biaryl urea moieties (12d and 15c) exhibited IC50 values of 11.9 and 13.6 nM respectively. Additionally, most of the newly synthesized final compounds were tested on 60

  血管内皮生长因子受体2（VEGFR-2）在癌症血管生成中起着至关重要的作用。在当前的研究中，根据已知II型VEGFR-2抑制剂的结构活性关系（SAR）研究，设计并合成了一系列新型的基于吡咯并[2,3- d ]嘧啶的化合物作为VEGFR-2抑制剂。 。评价了新合成的化合物在体外抑制VEGFR-2激酶的能力。所有测试的化合物均表现出高度有效的剂量相关的VEGFR-2抑制作用，IC 50值在纳摩尔范围内。在这些化合物中，带有联芳基尿素部分（12d和15c）的吡咯并[2,3- d ]嘧啶衍生物表现出IC50个值分别为11.9和13.6 nM。此外，大多数新合成的最终化合物已在60种人类癌细胞系中进行了测试。进行了将这些化合物对接成VEGFR-2的非活性构象，这显示了与FDA批准的VEGFR-2激酶抑制剂相当的结合模式。这些新发现的有效激酶抑制剂可被视为开发新的靶向抗癌剂的潜在候选药物。
• Substituted cyclic amine compound, production process thereof and
  申请人：Toa Eiyo, Ltd.

  公开号：US05728835A1

  公开（公告）日：1998-03-17

  A substituted cyclic amine compound represented by the following general formula (1) ##STR1## wherein each of R.sup.1 to R.sup.5 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or the like, A represents a carbonyl group or a sulfonyl group, B represents a methine moiety or a nitrogen atom, D represents a methine moiety, a nitrogen atom or .dbd.N(.fwdarw.O)-- and n is an integer of 2 to 3; and synthetic methods thereof. The inventive compound is useful in preventing and treating circulatory organ-related diseases such as hypertension, ischemic heart disease, cerebrovascular disease, peripheral circulatory disease and the like.

  一种代表如下一般式（1）的替代环胺化合物 ##STR1## 其中R.sup.1到R.sup.5中的每一个代表氢原子、卤素原子、低烷基、低烷氧基或类似物，A代表羰基或磺酰基，B代表亚甲基团或氮原子，D代表亚甲基团、氮原子或.dbd.N(.fwdarw.O)--，n为2至3的整数；以及其合成方法。这种创新化合物在预防和治疗循环系统相关疾病，如高血压、缺血性心脏病、脑血管疾病、周围循环疾病等方面具有用处。