4-iodobenzenediazonium chloride | 20893-72-5

• 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-iodobenzenediazonium chloride
• 英文别名: diazotized 4-iodoaniline；4-iodo-benzenediazonium; chloride；4-Jod-benzoldiazonium; Chlorid；p-Iodophenyldiazonium chloride；4-iodobenzenediazonium;chloride
• CAS: 20893-72-5
• 化学式: C₆H₄IN₂*Cl
• 分子量: 266.469
• InChiKey: XCNWMZUPKAVKPM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.22
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-iodobenzenediazonium chloride 以30%的产率得到
  参考文献：
  名称：

  YAMBUSHEV, F. D.;KOVYRZINA, V. P.;SHAGIDULLIN, R. R.;GORCHAKOVA, L. A.;FE+, ZH. OBSHCH. XIMII, 1981, 51, N 10, 2232-2241

  摘要：

  DOI：
• 作为产物：
  描述：

  4-碘苯胺盐酸盐 在 sodium nitrite 作用下， 以 水 为溶剂， 生成 4-iodobenzenediazonium chloride
  参考文献：
  名称：

  Novel azo dyes derived from 8-methyl-4-hydroxyl-2-quinolone: Synthesis, UV–vis studies and biological activity

  摘要：

  In this study, N,N'-di-(2-methylphenyl)malonamide was synthesized and reacted with polyphosphoric acid to afford 8-methyl-4-hydroxyl-2-quinolone. Eight novel azo disperse dyes were then synthesized by linking diazotized p-substituted aniline derivatives with 8-methyl-4-hydroxyl-2-quinolone. The solvatochromism of these azo dyes in various solvents was evaluated. All the compounds were then evaluated for their antibacterial activity against four bacteria, namely, Bacillus subtilis, Micrococcus luteus, Salmonella enterica, and Pseudomonas aeruginosa. The results showed that some of these compounds have high levels of antibacterial activity. (C) 2013 E.O. Moradi Rufchahi. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.03.002

文献信息

• Synthesis, <i>in Vitro</i> and <i>in Silico</i> Studies of Some Novel 5-Nitrofuran-2-yl Hydrazones as Antimicrobial and Antitubercular Agents
  作者：Hatem Abdel-Kader Abdel-Aziz、Wagdy Mohamed Eldehna、Mohamed Fares、Tilal Elsaman、Marwa Mostafa Abdel-Aziz、Dalia Hussein Soliman

  DOI：10.1248/bpb.b15-00439

  日期：——

  In this study, we synthesized two series of novel 5-nitrofuran-2-carbohydrazides 21a–h and 22a–e in addition to a third series of thiophene-2-carbohydrazides 23a–g to develop potent antimicrobial and/or antitubercular agents. The newly synthesized compounds were evaluated in vitro for their antimicrobial and antimycobacterial activities. Most of the 5-nitrofuran-2-carbohydrazides 21a–h and 22a–e displayed variable activity against Aspergillus fumigates, Staphylococcus aureus, Streptococcus pneumonia, Bacillis subtilis, Salmonella typhimurium, Klebsiella pneumonia, Escherichia coli and Mycobacterium tuberculosis. The sulfonamide derivative 21f exhibited superior potency and broad-spectrum antimicrobial activity with minimum inhibitory concentration (MIC)=0.06–0.98 µg/mL and antimycobacterial activity with MIC=3.9 µg/mL. The 5-nitrofuran-2-carbohydrazides 21a, b, g, h and 22a–c exhibited significant antibacterial activity with MIC values in the range of 0.12–7.81 µg/mL. The significances of the 5-nitrofuran moiety and sulfonamide function were explored via the structure–activity relationship (SAR) study. In addition, docking studies revealed that the p-amino benzoic acid (PABA) and binding pockets of the dihydropteroate synthase (DHPS) were successfully occupied by compound 21f. Furthermore, two quantitative structure–activity relationship (QSAR) models were built to explore the structural requirements which controlled the activity.

  在本研究中，我们合成了两系列新型5-硝基呋喃-2-甲酰肼21a–h和22a–e，以及第三系列噻吩-2-甲酰肼23a–g，旨在开发强效抗菌和/或抗结核剂。新合成的化合物在体外进行了抗菌和抗分枝杆菌活性评估。大多数5-硝基呋喃-2-甲酰肼21a–h和22a–e对烟曲霉、金黄色葡萄球菌、肺炎链球菌、枯草芽孢杆菌、鼠伤寒沙门氏菌、肺炎克雷伯菌、大肠埃希菌和结核分枝杆菌显示出不同程度的活性。磺胺衍生物21f表现出优越的广谱抗菌活性，最小抑制浓度（MIC）=0.06–0.98 µg/mL，以及抗分枝杆菌活性，MIC=3.9 µg/mL。5-硝基呋喃-2-甲酰肼21a、b、g、h和22a–c显示出显著的抗菌活性，MIC值在0.12–7.81 µg/mL范围内。通过结构-活性关系（SAR）研究探讨了5-硝基呋喃部分和磺胺功能的重要性。此外，对接研究揭示了化合物21f成功占据了对氨基苯甲酸（PABA）和二氢蝶酸合酶（DHPS）的结合口袋。进一步地，构建了两个定量结构-活性关系（QSAR）模型，以探索控制活性的结构要求。
• A Convenient Conversion of Substituted Cyclohexenones into Aryl Methyl Ketones
  作者：Franz Bracher、André Gehring

  DOI：10.1055/s-0032-1316560

  日期：2012.8

  bi- and tricyclic aryl methyl ketones in one single working process. Crucial steps are the addition of 1-ethoxyvinyllithium to the carbonyl group, followed by acid-catalyzed enol ether hydrolysis, dehydration, and dehydrogenation. This work describes a straightforward multistep conversion of substrates containing a cyclohexenone moiety into mono-, bi- and tricyclic aryl methyl ketones in one single working

  摘要 这项工作描述了在一个单一的工作过程中，将包含环己烯酮部分的底物直接多步转化为单环，双环和三环芳基甲基酮的过程。关键步骤是将1-乙氧基乙烯基锂加到羰基上，然后进行酸催化的烯醇醚水解，脱水和脱氢。 这项工作描述了在一个单一的工作过程中，将包含环己烯酮部分的底物直接多步转化为单环，双环和三环芳基甲基酮的过程。关键步骤是将1-乙氧基乙烯基锂加到羰基上，然后进行酸催化的烯醇醚水解，脱水和脱氢。
• Nitrogen bridgehead compounds. Part 18. New antiallergic 4H-pyrido[1,2-a]pyrimidin-4-ones. Part I
  作者：Istvan Hermecz、Tibor Breining、Zoltan Meszaros、Agnes Horvath、Lelle Vasvari-Debreczy、Franz Dessy、Christine DeVos、Ludovic Rodriquez

  DOI：10.1021/jm00352a008

  日期：1982.10

  A new type of antiallergic agent, 9-hydrazono-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-ones, was synthesized and evaluated for inhibitory effects in the rat reagenic passive cutaneous anaphylaxis (PCA) screen. Several racemic 6-methyl derivatives were found to be more potent than disodium chromoglycate intravenously and some were also active orally. Structure-activity relationships are discussed

  合成了一种新型的抗过敏药9-肼基-6,7,8,9-四氢-4H-吡啶并[1,2-a]嘧啶-4-酮，并评估了其对大鼠自发性被动皮肤的抑制作用。过敏反应（PCA）屏幕。已发现几种消旋的6-甲基衍生物在静脉内比色甘氨酸二钠更有效，有些还具有口服活性。讨论了构效关系。在具有6S和6R绝对构型的对映异构体之间的6-甲基系列中观察到高立体特异性，前者更具活性。化合物17，（+）-6（S）-甲基-9-（苯肼基）-4-氧代-4H-吡啶并[1,2-a]嘧啶-3-羧酸[Chinoin-1045; [UCB L140]，ED50值为1.0 mumol / kg po，目前正在临床研究中。
• [EN] 4-ARYLAZO-3,5-DIAMINO-PYRAZOLE COMPOUNDS AND USE THEREOF<br/>[FR] COMPOSES DE 4-ARYLAZO-3,5-DIAMINO-PYRAZOLE ET LEUR UTILISATION
  申请人：INST OF EX BOTANY OF THE ACADE

  公开号：WO2006024858A1

  公开（公告）日：2006-03-09

  A series of mono- and binuclear 4-arylazo-3,5-diamino-pyrazoles which are useful for inhibition of cyclin-dependent kinases (preferably CDK9). Hence they can be used as antimitotic-, pro-apoptotic and antünflammatory drugs, in particular, in chemotherapy of cancer and asthma, therapy of psoriasis and parasitoses as those caused by fungi or protists, treatment of Alzheimer's disease or as antineurodegenerative drugs, or to suppress immunostimulation. These compounds are useful in a variety of utilities, including as intermediates in the preparation of flame-retardants, diagnostic reagents and therapeutics, including antivirals and immunosuppressors.

  一系列单核和双核的4-芳基偶氮-3,5-二氨基吡唑醇，可用于抑制细胞周期依赖性激酶（优选为CDK9）。因此，它们可以用作抗有丝分裂、促凋亡和抗炎药物，特别是在癌症和哮喘化疗、牛皮癣和由真菌或原生动物引起的寄生虫病的治疗中，阿尔茨海默病的治疗或作为抗神经退行性药物，或用于抑制免疫刺激。这些化合物在各种用途中都很有用，包括作为制备阻燃剂、诊断试剂和治疗药物的中间体，包括抗病毒药物和免疫抑制剂。
• Synthesis of novel 5-substituted phenyl-3-(p-isopropylphenyl)-1-phenylformazan and their biological activities
  作者：Ayşe ŞAHİN YAĞLIOĞLU、Hülya ŞENÖZ

  DOI：10.3906/kim-1612-42

  日期：——

  Novel 1-substituted 3-(p-isopropylphenyl)-5-phenylformazans (3a--g) were synthesized and characterized by elemental analysis, $^1}$H NMR, and FT-IR techniques and UV-visible spectroscopy. Antiproliferative activities of 3a--g against HeLa and C6 cells were determined using the BrdU cell proliferation ELISA assay. 5-Florouracil was used as the positive control. The effects of substituents (--H, --CH$_3}$, and --I) and their positions ($ortho$, $meta$, and $para$) on the antiproliferative activities were evaluated. The results of the assay indicate that I substituent exhibited higher activity against the cells at the $meta$ and $para$ positions than --CH$_3}$ and --H substituents. 3a--g exhibited both high antiproliferative activities against C6 cells and noncytotoxicity. 3a--g may be anticancer drug candidates.

  合成了新型1-取代的3-(对异丙基苯基)-5-苯基偶氮化合物（3a-g），并通过元素分析、$^1}$H NMR、FT-IR技术及紫外-可见光光谱进行了表征。使用BrdU细胞增殖ELISA测定了3a-g对HeLa和C6细胞的抗增殖活性。5-氟尿嘧啶被用作阳性对照。评估了取代基（--H、--CH$_3}$和--I）及其在($ortho$、$meta$和$para$）位置上对抗增殖活性的影响。实验结果表明，I取代基在$meta$和$para$位点对细胞表现出比--CH$_3}$和--H取代基更高的活性。3a-g对C6细胞表现出较高的抗增殖活性且无细胞毒性。3a-g可能是抗癌药物候选物。