Oroidin | 203399-38-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Oroidin
• 英文别名: oroidin hydrochloride；Oroidin hydrochloride；N-[(E)-3-(2-amino-1H-imidazol-5-yl)prop-2-enyl]-4,5-dibromo-1H-pyrrole-2-carboxamide;hydrochloride
• CAS: 203399-38-6
• 化学式: C₁₁H₁₁Br₂N₅O*ClH
• 分子量: 425.51
• InChiKey: VECNMAOSMHEWJB-TYYBGVCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  99.6
• 氢给体数：
  5
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Oroidin 、 N-[(E)-3-(2-氨基-3H-咪唑-4-基)丙-2-烯基]-4,5-二溴-1H-吡咯-2-甲酰胺 、 三氟乙酸 以 六甲基磷酰三胺 、 甲醇 、 水 为溶剂， 反应 5.5h， 以2%的产率得到N-[3-[2-amino-4-[(E)-1-(2-amino-1H-imidazol-5-yl)-3-[(4,5-dibromo-1H-pyrrole-2-carbonyl)amino]prop-1-enyl]-1H-imidazol-5-yl]propyl]-4,5-dibromo-1H-pyrrole-2-carboxamide;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  Unprecedented Biomimetic Homodimerization of Oroidin and Clathrodin Marine Metabolites in the Presence of HMPA or Phosphonate Salt Tweezers

  摘要：

  The first biomimetic homodimerization of oroidin and clathrodin was effected in the presence HMPA and diphosphonate salts, strong guanidinium and amide chelating agents. The intermolecular associations probably interfere with the entropically and kinetically favored intramolecular cyclizations. Use of oroidin.1/2HCl salt or clathrodin.1/2HCl was indicative in the presence of the ambident nucleophilic and electrophilic tautomers of the 2-aminoimidazolic oroidin and clathrodin precursors. Surprisingly, the homodimerization of oroidin led to the nagelamide D skeleton, while the homodimerization of clathrodin gave the benzene para-symmetrical structure 19. The common process was rationalized from tautomeric precursors I and III.

  DOI：

  10.1021/np400048r
• 作为产物：
  描述：

  cis-oroidin acetate 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以44%的产率得到Oroidin
  参考文献：
  名称：

  Synthesis of substituted heterocyclic compounds

  摘要：

  本发明涉及一种合成杂环化合物的方法。本发明的特点在于，它包括打开一个具有公式（I）的化合物，其中：-X代表NH、O、S或N-p基团，p是保护基团，例如Boc或Troc；-Y代表N、O、S；-Z代表NH2或NH-p；以及-R1代表C1-C6烷氧基、芳氧基（例如苯氧基）或吡咯基，这些基团可以选择性地被取代，或它们的盐和上述化合物的异构体。此外，上述打开步骤在条件下进行，以产生具有公式（II）的杂环，其中：-X、Y和Z如上所定义；-R2代表-CH═CH-CH2-NH-COR1或-CH═CH-CH2-NH-CO基团；而R3占据一个、两个或三个位置，并表示卤素。本发明可用于合成天然产物。

  公开号：

  US20070106077A1

文献信息

• Synthesis of substituted heterocyclic compounds
  申请人：Al Mourabit Ali

  公开号：US20070106077A1

  公开（公告）日：2007-05-10

  The invention relates to a method of synthesizing heterocyclic compounds. The invention is characterised in that it consists in opening a compound having formula (I), wherein: —X represents NH, O, S or a N-p group, p being a protective group, such as Boc or Troc; —Y represents N, O, S; -Z represents NH 2 or NH-p; and —R 1 represents a C 1 -C 6 alkoxy radical, aryloxy, such as phenyloxy, or a pyrrolyl radical, said radicals being optionally substituted, or the salts thereof, and the isomers of the aforementioned compounds. Moreover, the above-mentioned opening step is performed in conditions such as to produce a heterocycle having formula (II), wherein: —X, Y and Z are as defined above; —R 2 represents a —CH═CH—CH 2 —NH—COR 1 or —CH═CH—CH 2 —NH—CO group; and R 3 occupies one, two or three positions and represents a halogen. The invention can be used to synthesise natural products.

  本发明涉及一种合成杂环化合物的方法。本发明的特点在于，它包括打开一个具有公式（I）的化合物，其中：-X代表NH、O、S或N-p基团，p是保护基团，例如Boc或Troc；-Y代表N、O、S；-Z代表NH2或NH-p；以及-R1代表C1-C6烷氧基、芳氧基（例如苯氧基）或吡咯基，这些基团可以选择性地被取代，或它们的盐和上述化合物的异构体。此外，上述打开步骤在条件下进行，以产生具有公式（II）的杂环，其中：-X、Y和Z如上所定义；-R2代表-CH═CH-CH2-NH-COR1或-CH═CH-CH2-NH-CO基团；而R3占据一个、两个或三个位置，并表示卤素。本发明可用于合成天然产物。
• Unprecedented Biomimetic Homodimerization of Oroidin and Clathrodin Marine Metabolites in the Presence of HMPA or Phosphonate Salt Tweezers
  作者：Clarisse Lejeune、Hua Tian、Jérôme Appenzeller、Ludmila Ermolenko、Marie-Thérèse Martin、Ali Al-Mourabit

  DOI：10.1021/np400048r

  日期：2013.5.24

  The first biomimetic homodimerization of oroidin and clathrodin was effected in the presence HMPA and diphosphonate salts, strong guanidinium and amide chelating agents. The intermolecular associations probably interfere with the entropically and kinetically favored intramolecular cyclizations. Use of oroidin.1/2HCl salt or clathrodin.1/2HCl was indicative in the presence of the ambident nucleophilic and electrophilic tautomers of the 2-aminoimidazolic oroidin and clathrodin precursors. Surprisingly, the homodimerization of oroidin led to the nagelamide D skeleton, while the homodimerization of clathrodin gave the benzene para-symmetrical structure 19. The common process was rationalized from tautomeric precursors I and III.