(Z)-4-methoxy-(2,2'-bipyridine)-6-carboxaldehyde oxime | 102116-97-2

• 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: (Z)-4-methoxy-(2,2'-bipyridine)-6-carboxaldehyde oxime
• 英文别名: (Z)-4-methoxy-2,2'-bipyridine-6-carbaldehyde oxime；(Z)-4-methoxy-2,2'-bipyridyl-6-aldoxime；caerulomycin A；Carulomycin A；(NZ)-N-[(4-methoxy-6-pyridin-2-ylpyridin-2-yl)methylidene]hydroxylamine
• CAS: 102116-97-2
• 化学式: C₁₂H₁₁N₃O₂
• 分子量: 229.238
• InChiKey: JCTRJRHLGOKMCF-ZSOIEALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ferrous ammonium sulphate 、 sodium perchlorate 、 (Z)-4-methoxy-(2,2'-bipyridine)-6-carboxaldehyde oxime 在 NaOH 作用下， 以 乙醇 为溶剂， 生成 [Fe(C₁₀N₂H₆(OCH₃)(CHNO))2]*3H₂O 、 [Fe(C₅H₄NC₅H₂N(OCH₃)(CHNOH))(C₅H₄NC₅H₂N(OCH₃)(CHNO))]⁽¹⁺⁾*[ClO₄]^(1-)*H₂O=[Fe(C₁₀N₂H₆(OCH₃)(CHNO))2H](ClO₄)*H₂O
  参考文献：
  名称：

  N-杂环分子复合物中的平衡。第34部分：铁与铜霉素的结合

  摘要：

  讨论了具有铁（II）的铜霉素（Hcmn）配合物的光谱性质。络合物的化学计量（乔布法）为2 cmn：1 Fe; cmn充当一个齿状配体。红色[Fe（Hcmna）（cmna）] +（Hcmna =铜霉素A）形成紫色共轭碱[Fe（cmna）2 ]的p K a为3.5。制得既包含红色阳离子又包含紫色不带电物质的固体化合物。据报道，青霉素D及其铁（II）配合物具有可见的cd光谱。

  DOI：

  10.1039/dt9840002245
• 作为产物：
  描述：

  2,2′-二吡啶基 N-氧化物 在 吡啶 、 正丁基锂 、 四甲基乙二胺 、 硫酸 、 盐酸羟胺 、 三溴化磷 、 potassium nitrate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 氯仿 为溶剂， 反应 25.5h， 生成 (Z)-4-methoxy-(2,2'-bipyridine)-6-carboxaldehyde oxime
  参考文献：
  名称：

  First Syntheses of Caerulomycin E and Collismycins A and C. A New Synthesis of Caerulomycin A

  摘要：

  Caerulomycins produced by Streptomyces caeruleus, and collismycins more recently isolated from Streptomyces species, are bipyridinic molecules endowed with antibiotic and cytotoxic activities. The first syntheses of caerulomycin E (1), as well as new syntheses of caerulomycin A (2), are reported. Methodologies involving efficiently controlled reactions such as metalation and cross-coupling reactions have been developed from 2,2'-bipyridine. The functionalization at C-6 could be achieved by metalation of 2,2'-bipyridine N-oxides 5 and 12. 6-Halo-4-methoxy-2,2'-bipyridines (6, 10, 11) became key-molecules of these different pathways, and further functionalization at C-5 allowed the first syntheses of collismycins A (3) and C (4).

  DOI：

  10.1021/jo972022i

文献信息

• 4-Methoxy-2,2'-bipyridyl-6-aldoxime, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als Arzneimittel
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0159640A1

  公开（公告）日：1985-10-30

  Die vorliegende Erfindung betrifft die Verbindung 4-Methoxy-2,2'-bipyridyl-6-aldoxim und Isomere und ein Verfahren sowie Zwischenprodukte zu dessen Herstellung. Die Verbindungen können bei der Behandlung von Krankheiten, die durch Bakterien oder Amöben hervorgerufen werden, verwendet werden.

  本发明涉及 4-甲氧基-2,2'-联吡啶-6-醛肟及其异构体，以及制备该化合物的工艺和中间体。 该化合物可用于治疗由细菌或变形虫引起的疾病。
• Alreja, Bipin D.; Kattige, Samba L.; Lal, Bansi, Heterocycles, 1986, vol. 24, # 6, p. 1637 - 1640
  作者：Alreja, Bipin D.、Kattige, Samba L.、Lal, Bansi、Souza, Noel J. de

  DOI：——

  日期：——
• ALREJA, BIPIN, DHIRAJLAL;KATTIGE, SAMBA, LAXMINARAYAN;SOUZA, N. J.
  作者：ALREJA, BIPIN, DHIRAJLAL、KATTIGE, SAMBA, LAXMINARAYAN、SOUZA, N. J.

  DOI：——

  日期：——
• Cytotoxic Bipyridines from the Marine-Derived Actinomycete <i>Actinoalloteichus cyanogriseus</i> WH1-2216-6
  作者：Peng Fu、Shuxia Wang、Kui Hong、Xia Li、Peipei Liu、Yi Wang、Weiming Zhu

  DOI：10.1021/np200258h

  日期：2011.8.26

  Five new bipyridine alkaloids (1-5) and a new phenylpyridine alkaloid (6), which we name caerulomycins F-K, along with five known analogues (7-11), were isolated from the marine-derived actinomycete Actinoalloteichus cyanogriseus WH1-2216-6. The structures of 1-6 were established on the basis of spectroscopic analyses and chemical methods. Compounds 1-10 showed cytotoxicity against the HL-60, K562, KB, and A549 cell lines, with IC50 values of 0.26 to 15.7 mu M. Compounds 7 and 8 also showed antimicrobial activities against Escherichia coli, Aerobacter aerogenes, Pseudomonas aeruginosa, and Candida albicans, with MIC values of 9.7 to 38.6 mu M.
• First Syntheses of Caerulomycin E and Collismycins A and C. A New Synthesis of Caerulomycin A
  作者：François Trécourt、Bruno Gervais、Olivier Mongin、Catherine Le Gal、Florence Mongin、Guy Quéguiner

  DOI：10.1021/jo972022i

  日期：1998.5.1

  Caerulomycins produced by Streptomyces caeruleus, and collismycins more recently isolated from Streptomyces species, are bipyridinic molecules endowed with antibiotic and cytotoxic activities. The first syntheses of caerulomycin E (1), as well as new syntheses of caerulomycin A (2), are reported. Methodologies involving efficiently controlled reactions such as metalation and cross-coupling reactions have been developed from 2,2'-bipyridine. The functionalization at C-6 could be achieved by metalation of 2,2'-bipyridine N-oxides 5 and 12. 6-Halo-4-methoxy-2,2'-bipyridines (6, 10, 11) became key-molecules of these different pathways, and further functionalization at C-5 allowed the first syntheses of collismycins A (3) and C (4).