diazotated 3-iodoaniline | 20893-75-8

• 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: diazotated 3-iodoaniline
• 英文别名: 3-iodobenzenediazonium;chloride
• CAS: 20893-75-8
• 化学式: C₆H₄IN₂*Cl
• 分子量: 266.469
• InChiKey: LXJRNPKTLUFUBG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.22
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.15
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  diazotated 3-iodoaniline 在 [RuHCl(CO)(PPh₃)₃] 、 sodium acetate 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  取代二苯重氮的一般方法

  摘要：

  已开发出一种基于经典偶氮偶合反应的不对称取代的二苯基二氮杂烯的通用合成方法。该方法的关键特征是使用N，N-二烯丙基保护的苯胺衍生物作为偶联组分。偶联组分的N，N-二烯丙基部分保证足够的反应性，并允许避免由中间三氮烯形成导致的结构异构体的形成。此外，在偶联反应之后，N，N-二烯丙基氨基官能团可以通过重氮离子中间体被包括氢在内的其他取代基取代。通常，采用这种方法可以以合理的收率获得目标化合物。

  DOI：

  10.1016/j.tet.2016.02.011
• 作为产物：
  描述：

  3-碘苯胺 在 盐酸 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 生成 diazotated 3-iodoaniline
  参考文献：
  名称：

  取代二苯重氮的一般方法

  摘要：

  已开发出一种基于经典偶氮偶合反应的不对称取代的二苯基二氮杂烯的通用合成方法。该方法的关键特征是使用N，N-二烯丙基保护的苯胺衍生物作为偶联组分。偶联组分的N，N-二烯丙基部分保证足够的反应性，并允许避免由中间三氮烯形成导致的结构异构体的形成。此外，在偶联反应之后，N，N-二烯丙基氨基官能团可以通过重氮离子中间体被包括氢在内的其他取代基取代。通常，采用这种方法可以以合理的收率获得目标化合物。

  DOI：

  10.1016/j.tet.2016.02.011

文献信息

• 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。
• 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。
• Theoretical studies of the tautomerism in 3-(2-R-Phenylhydrazono)-naphthalene- 1,2,4-triones: synthesis of copper(II) complexes and studies of antibacterial and antitumor activities
  作者：Acácio I. Francisco、Maria D. Vargas、Thaís P. Fragoso、J. Walkimar de M. Carneiro、Annelise Casellato、Fernando de C. da Silva、Vitor F. Ferreira、Jussara P. Barbosa、Claudia Pessoa、Letícia V. Costa-Lotufo、José D. B. Marinho Filho、Manoel O. de Moraes、Antonio S. Mangrich

  DOI：10.1590/s0103-50532010000700017

  日期：——

  DFT calculations using the B3LYP and PBE1PBE functionals with the standard 6-31G(d) and 6-311+G(2d,p) basis sets were carried out for the 3-(2-phenylhydrazone)-naphthalene-1,2,4-trione system in solution (dmso) and in the gas phase, and showed the keto-hydrazone forms (rotamers Ia and Ib) to be more stable than the enol-azo forms (rotamers IIa and IIb, by about 14 kcal mol(-1)) and III (by approximately 6 kcal mol(-1)), independently of the nature of the substituent in the phenylene ring. These results were confirmed by spectroscopic data on the derivatives HL1-HL13, obtained from 2-hydroxy-1,4-naphthoquinone and arylamines (R = 4-OMe, 4-N-2-C6H5, 4-Cl, 4-I, 3-I, 2-I, 4-COOH, 3-COOH, 4-CN, 3-CN, 4-NO2, 3-NO2, 2-NO2). The in vitro antitumor (against SF-295, HCT-8, MDAMB-435 and HL-60 cancer cell lines) and antibacterial activities (Bacillus cereus, Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Klebsiella pneumonia and Pseudomonas aeruginosa) of compounds HL1-HL13 and of their respective copper(II) complexes, [Cu(L1-13)(2)], were tested. In general, these compounds exhibited low antibacterial activity, except for HL5 (R = 3-I), more active than the control; however, the corresponding complex was inactive. In contrast, increased cytotoxicity was observed upon complexation. Complex [Cu(L13)(2)] (R = 3-NO2) presented moderate cytotoxicity against human leukemia (HL-60).
• HERMECZ, I.;BREINING, T.;MESZAROS, Z.;HORVATH, A.;VASVARI-DEBRECZY, L.;DE+, J. MED. CHEM., 1982, 25, N 10, 1140-1145
  作者：HERMECZ, I.、BREINING, T.、MESZAROS, Z.、HORVATH, A.、VASVARI-DEBRECZY, L.、DE+

  DOI：——

  日期：——