4-chloro-2-nitrophenyl azide | 89284-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chloro-2-nitrophenyl azide
• 英文别名: 2-nitro-4-chloro-phenylazide；1-Azido-4-chloro-2-nitrobenzene
• CAS: 89284-67-3
• 化学式: C₆H₃ClN₄O₂
• 分子量: 198.568
• InChiKey: WIRNSUXJXYSMIL-UHFFFAOYSA-N

物化性质

• 熔点：
  61-62 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-2-nitrophenyl azide 在 吗啉 、 hydrazine hydrate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 7-chloro-3-methyl-1,4-dioxy-quinoxaline-2-carboxylic acid hydrazide
  参考文献：
  名称：

  Synthesis and Characterization of Newly Fused 1,2-Dihydropyrido[3,4-b], Bridged Oxadiazol-2-yl, 4-Substituted-benzylidene Hydrazide and Arylidene 6-Chloroquinoxaline 1,4-Dioxides

  摘要：

  Some simple reactions using commercially available chemicals were used in the preparation of new biologically remarkable quinoxaline 1,4-dioxide derivatives. Several steps performed on 4-chloro-2-nitroaniline resulted in a quinoxaline 1,4-dioxide derivative, which reacted with dimethylformamide dimethylacetal (DMF-DMA) to produce an enamine. Transamination of this enamine with anilines gave the fused 1,2-dihydropyrido[3,4-b] quinoxaline 5,10-dioxide derivatives via an addition-elimination mechanism. Basic condensation reaction of quinoxaline active methyl afforded unexpected decarboxylated arylidene derivatives by using different aromatic aldehydes. Bridged oxadiazol-2-yl derivatives were obtained from the reaction of a hydrazide derivative with carbon disulfide and p-nitrobenzoic acid respectively. Whereas, acidic condensation of that hydrazide with aromatic aldehydes afforded the arylidene hydrazides.

  DOI：

  10.21577/0103-5053.20180081
• 作为产物：
  描述：

  N-(4-氯-2-硝基苯基)乙酰胺 在 盐酸 、 sodium azide 、 硫酸 、 sodium acetate 、 sodium nitrite 作用下， 反应 0.5h， 生成 4-chloro-2-nitrophenyl azide
  参考文献：
  名称：

  Hypoxia-Selective Agents Derived from Quinoxaline 1,4-Di-N-oxides

  摘要：

  Hypoxic cells, which are a common feature of solid tumors, but not normal tissues, are resistant to both anticancer drugs and radiation therapy. Thus the identification of drugs with selective toxicity toward hypoxic cells is an important objective in anticancer chemotherapy. The benzotriazine di-N-oxide (SR 4233, Tirapazamine) has been shown to be an efficient and selective cytotoxin for hypoxic cells. Since the bioreductive activation of Tirapazamine is thought to be due to the presence of the 1,4-di-N-oxide moiety, a series of 3-aminoquinoxaline-2-carbonitrile 1,4-di-N-oxides with a range of electron-donating and -withdrawing substituents in the 6- and/or 7- positions has been synthesized and evaluated for toxicity to hypoxic cells. Electrochemical studies of the quinoxaline di-N-oxides and Tirapazamine showed that as the electron-withdrawing nature of the 6(7)-substituent increases, the reduction potential becomes more positive and the compound is more readily reduced. Apart from the unsubstituted 6a and the 6,7-dimethyl derivative 6c, the quinoxaline di-N-oxides have reduction potentials significantly more positive than Tirapazamine (E(pc)-0.90 V). The most potent cytotoxins to cells in culture were the 6,7,-dichloro and 6,7-difluoro derivatives 6i and 6l, which were 30-fold more potent than Tirapazamine. The 6(7)-fluoro and 6(7)-chloro compounds, 6e and 6h, showed the greatest hypoxia selectivity. Four of the compounds, 6e, 6f, 6h and 6i, killed the inner cells of multicellular tumor spheroids in vitro. In vivo Balb/c mice tolerated a dose of these four compounds twice the size of that of Tirapazamine. This study demonstrates that quinoxaline 1,4-di-N-oxides could provide useful hypoxia-selective therapeutic agents.

  DOI：

  10.1021/jm00010a023

文献信息

• Design, combinatorial synthesis and biological evaluations of novel 3-amino-1′-((1-aryl-1 H -1,2,3-triazol-5-yl)methyl)-2′-oxospiro[benzo[ a ] pyrano[2,3- c ]phenazine-1,3′-indoline]-2-carbonitrile antitumor hybrid molecules
  作者：Yuanyuan Lu、Linlin Wang、Xiaobing Wang、Tao Xi、Jianmin Liao、Zhixiang Wang、Feng Jiang

  DOI：10.1016/j.ejmech.2017.04.040

  日期：2017.7

  activity against the A549 cancer cell line with IC50 value of 5.4 μM. All compounds had low or no effect against L02 and HUVEC non-cancer cell lines. Compound 36 was further confirmed to mainly locate mitochondria in A549 cancer cells via laser-scanning confocal microscopy. Moreover, compound 36 was proved to increase ROS production and induce cell cycle arrest in S phase. Western blot analysis illustrated

  59个新颖的3-氨基-1'-（（（1-芳基-1H-1,2,3-三唑-5-基）甲基）-2'-氧螺环[苯并[a]吡喃]的组合化学文库[本研究构建了设计为吩嗪，吡喃，吲哚和1,2,3-三唑药效团的杂合分子的2,3-c]吩嗪-1,3'-二氢吲哚] -2-腈。细胞毒性评估表明，某些化合物在体外对HCT116，MCF7，HepG2和A549癌细胞表现出中等的细胞毒性，其中化合物36被发现对A549癌细胞具有最佳的抗增殖活性，IC50值为5.4μM。所有化合物对LO2和HUVEC非癌细胞系均具有低或无作用。通过激光扫描共聚焦显微镜进一步证实了化合物36主要位于A549癌细胞中的线粒体。而且，化合物36被证明可以增加ROS的产生并诱导S期细胞周期停滞。Western blot分析表明，化合物36处理后，Bax / Bcl-2比值呈剂量依赖性增加，裂解的caspase-3和裂解的caspase-9均增强。上
• Design, synthesis and biological evaluation of novel 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole triazole derivatives as potent TRPV1 antagonists
  作者：Jinyu Li、Cunbin Nie、Yue Qiao、Jing Hu、Qifei Li、Qiang Wang、Xiaohui Pu、Lin Yan、Hai Qian

  DOI：10.1016/j.ejmech.2019.06.007

  日期：2019.9

  and had almost no hyperthermia side-effect. Furthermore, pharmacokinetic studies revealed that compound 6g had a superior oral exposure after oral administration in rats. To understand its binding interactions with the receptor, the docking study of 6g was performed in rTRPV1 model and showed an excellent fit to the binding site. On the basis of its superior profiles, 6g could be considered as the lead

  本文报道的是在以2,3,4,9-四氢-1 H-吡啶并[3,4- b ]吲哚为A区且三唑为B-的情况下构建的一类TRPV1拮抗剂的设计，合成和药理学评估。地区。SAR分析表明，与相应的二氢吲哚类似物相比，2,3,4,9-四氢-1 H-吡啶并[3,4- b ]吲哚类似物显示出对辣椒素激活hTRPV1的优异拮抗作用，并显示出更好的效价。该设计的优化导致最终鉴定出2-（（1-（2-（三氟甲基）苯基）-1 H -1,2,3-三唑-4-基）甲基）-2,3,4,9 -tetrahydro-1 H -pyrido [3,4- b ]吲哚（6克），一种有效的TRPV1拮抗剂。在体外，使用表达重组人TRPV1通道的细胞，6g表现出被辣椒素激活的强烈拮抗作用（IC 50  = 0.075μM），并且仅部分阻断了TRPV1的酸激活。在体内，6g在辣椒素诱导和热诱导的疼痛模型中显示出良好的疗效，并且几乎没有热疗的副
• Synthesis of 1,2,3 triazole‐linked pyrimidines catalyzed by mg‐Al‐LDH‐immobilized‐CuI as a heterogeneous catalyst
  作者：Fatemeh Rezaeimanesh、Mohammad Bakherad、Hossein Nasr‐Isfahani、Bahram Bahramian、Soheila Naderi

  DOI：10.1002/jhet.3772

  日期：2020.2

  A useful and efficient procedure was obtained for the synthesis of 1,2,3‐triazole‐linked pyrimidines via click reaction of propynylated pyrimidine and aromatic azides in the presence of Mg‐Al‐LDH‐immobilized‐CuI with high‐to‐excellent yields. Moreover, the prepared catalyst was characterized by the FT‐IR spectroscopy, XRD, BET, SEM, and ICP techniques. The developed synthetic technique offers numerous

  在Mg-Al-LDH固定化CuI存在下，通过丙烯酰化的嘧啶和芳族叠氮化合物的点击反应，可以高效，高效地合成1,2,3-三唑连接的嘧啶，并具有很高的产率。 。此外，通过FT-IR光谱，XRD，BET，SEM和ICP技术对制备的催化剂进行了表征。发达的合成技术具有许多优点，例如反应干净，后处理容易，反应产率高和反应时间短。
• Synthesis of 1,4‐Disubstituted 1,2,3‐Triazoles via 1,3‐Dipolar Cycloaddition/C–N Coupling of Propargyl Alcohols/amines and Aryl Azides
  作者：Mohammad Bakherad、Ahmad Kakavand Ghalenoei、Ali Keivanloo

  DOI：10.1002/jhet.3325

  日期：2018.12

  1,4‐Disubstituted 1,2,3‐triazoles are prepared through the 1,3‐dipolar cycloaddition of propargyl (alcohols/amines) and aryl azides in the presence of a mixture of Cu(OAc)2.H2O and NaAs as the catalyst. This method offers the advantages of mild experimental conditions, operational simplicity, and high‐to‐excellent reaction yields.

  1,4-二取代的1,2,3-三唑是在Cu（OAc）2 .H 2 O和NaAs的混合物存在下，通过炔丙基（醇/胺）和芳基叠氮化物的1,3-偶极环加成制备的作为催化剂。该方法具有温和的实验条件，操作简便和高至出色的反应收率的优点。
• 具有抗肿瘤活性的丹皮酚并苯并噁嗪类化合物及其制备方法和应用
  申请人：河南师范大学

  公开号：CN109761968A

  公开（公告）日：2019-05-17

  本发明公开了一种具有抗肿瘤活性的丹皮酚并苯并噁嗪类化合物及其制备方法和应用，属于抗肿瘤药物的合成技术领域。本发明的技术方案要点为：具有抗肿瘤活性的丹皮酚并苯并噁嗪类化合物，其结构式如下：本发明还公开了该化合物的制备方法及其应用。本发明合成过程简单、易于操作且成本低廉，还具有低污染的特点，合成的化合物可抑制人非小细胞肺癌细胞NCI‑H1299细胞和人宫颈癌HeLa细胞的生长，因而对人类研究肺腺癌以及宫颈癌的治疗起到至关重要的促进作用，使其在医药领域具有广阔的应用前景。