5-iodo-2-nitrosopyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-iodo-2-nitrosopyridine
• 化学式: C₅H₃IN₂O
• 分子量: 233.996
• InChiKey: XKZUJLMRNBSUET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 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：
  42.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-iodo-2-nitrosopyridine 、 麦角固醇 以 二氯甲烷 为溶剂， 反应 0.5h， 以82%的产率得到5,8-dihydro-8α,5α-(N-5-iodo-2-pyridinylepoxyimino)-ergosterol
  参考文献：
  名称：

  Syntheses and Biological Activity Studies of Novel Sterol Analogs from Nitroso Diels−Alder Reactions of Ergosterol

  摘要：

  A series of novel sterol analogs was prepared using nitroso Diels-Alder reactions with ergosterol. Most cycloaddition reactions proceeded in an excellent regio- and stereoselective fashion. Further N-O bond cleavage of cycloadducts generated compounds with biological activity in PC-3 and MCF-7 cancer cell lines.

  DOI：

  10.1021/ol900997t
• 作为产物：
  描述：

  2-氨基-5-碘吡啶 在 N-氯代丁二酰亚胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 5-iodo-2-nitrosopyridine
  参考文献：
  名称：

  Iminonitroso Diels−Alder Reactions for Efficient Derivatization and Functionalization of Complex Diene-Containing Natural Products

  摘要：

  A remarkably efficient method for derivatization of complex diene-containing natural products by using stabilized iminonitroso Diels-Alder reactions is described. Turimycin H3, ergosterol, reductiomycin, isoforocidin, colchicine and thebaine were found to react with nitrosopyridines in a highly efficient regio- and stereoselective fashion. Preliminary bioactivity evaluations of turimycin cycloadducts are reported.

  DOI：

  10.1021/ol071322b

文献信息

• N–O Chemistry for Antibiotics: Discovery of <i>N</i>-Alkyl-<i>N</i>-(pyridin-2-yl)hydroxylamine Scaffolds as Selective Antibacterial Agents Using Nitroso Diels–Alder and Ene Chemistry
  作者：Timothy A. Wencewicz、Baiyuan Yang、James R. Rudloff、Allen G. Oliver、Marvin J. Miller

  DOI：10.1021/jm200794r

  日期：2011.10.13

  The discovery, syntheses, and structure–activity relationships (SAR) of a new family of heterocyclic antibacterial compounds based on N-alkyl-N-(pyridin-2-yl)hydroxylamine scaffolds are described. A structurally diverse library of ∼100 heterocyclic molecules generated from Lewis acid-mediated nucleophilic ring-opening reactions with nitroso Diels–Alder cycloadducts and nitroso ene reactions with substituted

  描述了基于N-烷基-N- (吡啶-2-基)羟胺支架的新型杂环抗菌化合物家族的发现、合成和构效关系 (SAR) 。在全细胞抗菌试验中评估了由路易斯酸介导的亲核开环反应与亚硝基 Diels-Alder 环加合物和亚硝基烯与取代烯烃反应生成的约 100 个杂环分子的结构多样化文库。含有N-烷基-N- (吡啶-2-基)羟胺结构的化合物对革兰氏阳性细菌藤黄微球菌ATCC 10240 (MIC 90 ) 显示出选择性和有效的抗菌活性= 2.0 μM 或 0.41 μg/mL）并且对其他革兰氏阳性菌株具有中等活性，包括金黄色葡萄球菌(MRSA) 和粪肠球菌(VRE) 的抗生素耐药菌株。使用钯催化的N-烷基-O-（4-甲氧基苄基）羟胺与 2-卤代吡啶的Buchwald-Hartwig 胺化反应开发了一种新的活性核心合成路线，这促进了 SAR 研究并揭示了最简单的活性结构片段。这项工作显示了使用面向多样性的合成
• Preparation and biological evaluation of novel leucomycin analogs derived from nitroso Diels–Alder reactions
  作者：Baiyuan Yang、Tina Zöllner、Peter Gebhardt、Ute Möllmann、Marvin J. Miller

  DOI：10.1039/b922450e

  日期：——

  A series of 10,13-disubstituted 16-membered macrolides was synthesized using nitroso Diels–Alder reactions of leucomycin A7. Despite the extensive constituent functionalities in leucomycin, the hetero cycloaddition reactions proceeded in a highly regio- and stereoselective fashion. Subsequent chemical modifications of the nitroso cycloadducts, including N–O bond reduction, were also conducted. Most leucomycin derivatives retained antibiotic profiles similar to leucomycin A7, and, in contrast to leucomycin itself, several exhibited moderate antiproliferative and cytotoxic activity.

  利用白霉素 A7 的亚硝基 DielsâAlder 反应合成了一系列 10,13-二取代 16 元大环内酯类化合物。尽管白霉素中含有大量的组成官能团，但杂环加成反应仍以高度区域和立体选择性的方式进行。随后还对亚硝基环加成物进行了化学修饰，包括 NâO 键还原。大多数白霉素衍生物保留了与白霉素 A7 相似的抗生素特性，与白霉素本身不同的是，其中几种衍生物表现出适度的抗增殖和细胞毒性活性。
• Syntheses and Biological Activity Studies of Novel Sterol Analogs from Nitroso Diels−Alder Reactions of Ergosterol
  作者：Baiyuan Yang、Patricia A. Miller、Ute Möllmann、Marvin J. Miller

  DOI：10.1021/ol900997t

  日期：2009.7.2

  A series of novel sterol analogs was prepared using nitroso Diels-Alder reactions with ergosterol. Most cycloaddition reactions proceeded in an excellent regio- and stereoselective fashion. Further N-O bond cleavage of cycloadducts generated compounds with biological activity in PC-3 and MCF-7 cancer cell lines.
• Iminonitroso Diels−Alder Reactions for Efficient Derivatization and Functionalization of Complex Diene-Containing Natural Products
  作者：Fangzheng Li、Baiyuan Yang、Marvin J. Miller、Jaroslav Zajicek、Bruce C. Noll、Ute Möllmann、Hans-Martin Dahse、Patricia A. Miller

  DOI：10.1021/ol071322b

  日期：2007.7.1

  A remarkably efficient method for derivatization of complex diene-containing natural products by using stabilized iminonitroso Diels-Alder reactions is described. Turimycin H3, ergosterol, reductiomycin, isoforocidin, colchicine and thebaine were found to react with nitrosopyridines in a highly efficient regio- and stereoselective fashion. Preliminary bioactivity evaluations of turimycin cycloadducts are reported.