(+/-)-longamide | 219783-00-3

• 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: (+/-)-longamide
• 英文别名: rac-longamide A；(-)-longamide；longamide；6,7-dibromo-4-hydroxy-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one；6,7-dibromo-4-hydroxy-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-1-one
• CAS: 219783-00-3
• 化学式: C₇H₆Br₂N₂O₂
• mdl: MFCD25970428
• 分子量: 309.945
• InChiKey: NUVAABCZBKHWMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  54.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-longamide 在 sodium hydride 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成 6,7-dibromo-2-methyl-2H-pyrrolo[1,2-a]pyrazin-1-one
  参考文献：
  名称：

  通过三组分咪唑烷酮二元醇盐合成全细胞生长的海洋天然产物Dibromophakellstatin。

  摘要：

  来自海洋海绵Phakellia mauritiana的四环吡咯-咪唑生物碱二溴环已抑菌素已从吡咯经七个步骤合成，总收率为18％。关键步骤是三环烯酰胺，腈和氨基甲酰基结构单元的三组分组装，一步即可得到二溴环己汀的咪唑烷酮环。值得注意的是，可以将具有双重功能的试剂EtO 2 CNHOTs用作亲电子腈和偶极氨基甲酰基组分的来源。使用脱溴的前体双吡咯并吡嗪酮可以提高高得率，并允许我们开发第二代合成方法。确认了二溴泛函他汀的细胞抑制活性。

  DOI：

  10.1021/jo061813u
• 作为产物：
  描述：

  2,2,2-三氯-1-(4,5-二溴-1H-吡咯-2-基)-1-乙酮 在 盐酸 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 18.0h， 生成 (+/-)-longamide
  参考文献：
  名称：

  （±）-环鸟苷的全合成

  摘要：

  描述了（±）-cyclooroidin的第一个全合成，这是最近以光学纯净的形式从海绵Agelas oroides分离的吡咯-咪唑生物碱家族的成员。合成是通过9个线性步骤完成的，总收率为10％。关键步骤是对中间体长酰胺B进行Wolff溴酮合成。

  DOI：

  10.1016/j.tetlet.2005.10.060

文献信息

• Synthesis of Hydroxypyrrolone Carboxamides Employing Selectfluor
  作者：Tim Carlo Allmann、Rares-Petru Moldovan、Peter G. Jones、Thomas Lindel

  DOI：10.1002/chem.201503695

  日期：2016.1.4

  Reaction of pyrrole‐2‐carboxamides with Selectfluor in MeCN/water (4:1) affords 2‐hydroxy‐5‐oxopyrrole‐2‐carboxamides in yields of up to 80 %. A variety of sensitive functional groups is tolerated, among them aldehydes and alkynes. The new method also works in the presence of allyl groups and appears to be superior to the use of singlet oxygen. Reaction of the monobrominated dihydropyrrolo[1,2‐a]pyrazinone

  吡咯-2-羧酰胺与Selectfluor在MeCN /水中的反应（4：1）得到2-羟基-5-氧代吡咯-2-酮的酰胺，收率高达80％。可以耐受各种敏感的官能团，其中包括醛和炔烃。新方法也可在烯丙基存在下使用，并且似乎优于单线态氧的使用。的单溴化二氢吡咯并[1,2的反应一]吡嗪酮mukanadin C及其非溴化类似物，得到双环hydroxypyrrolones。这些化合物很有趣，因为它们构成了海洋天然产物氧代环苯乙烯基的一部分结构。
• Synthesis of the marine carbinolamine (+/−) longamide control of N-1 and C-3 bromopyrrole nucleophilicity
  作者：S. Marchais、A. Al Mourabit、A. Ahond、C. Poupat、P. Potier

  DOI：10.1016/s0040-4039(99)01092-8

  日期：1999.7

  examined. The ring-chain tautomerism involving a potential nucleophilicity of N1/C3 of bromopyrrole compounds has been examined. The behaviour of 7 in protic mild or in vigorous acidic conditions provides an entry to regioselective synthesis of marine polycycle alkaloids such as 2, 3, and 4. A biogenetic pathway is proposed for polycyclic 2-aminoimidazolopyrrole marine metabolites.

  描述了使用可能的仿生环化12的（+/-）长酰胺1的短合成。研究了其对映体形式的分离及其外消旋化。已经研究了涉及溴吡咯化合物的N 1 / C 3潜在亲核性的环链互变异构。7在质子性轻度或强烈酸性条件下的行为为海洋多环生物碱（如2、3和4）的区域选择性合成提供了一个入口。提出了多环2-氨基咪唑并吡咯海洋代谢物的生物遗传途径。
• ANNELATED CARBAMOYLASE-HETEROCYCLES, FOCUSED LIBRARY, PHARMACEUTICAL COMPOSITIONS AND METHODS FOR THE PRODUCTION THEREOF
  申请人："Chemical diversity Research Institute", Ltd.

  公开号：EP1746100A1

  公开（公告）日：2007-01-24

  This invention relates to novel annellated carbamyl-aza-heterocyclic compounds that are potential physiologically active compounds (agonists, antagonists, and receptor modulators, enzyme inhibitors, oncolytics, antibacterial and antiparasitic agents, and so on), to a focused library comprising annellated carbamyl-aza-heterocyclic compounds, a pharmaceutical composition comprising annellated carbamyl-aza-heterocyclic compounds as the active ingredient, and to methods of producing and using the same. The invention relates to annellated carbamyl-aza-heterocyclic compounds of general formula 1: wherein: W is 6-oxopiperazine, [1,4]diazepan, [1,4]thiazepan or [1,4]oxazepan compound annellated to at least one optionally substituted and optionally condensed heterocyclic compound Q; R1, R2 and R3 are, independently of one another, a hydrogen atom, an inert substituent, an optionally substituted C1-C6 alkyl, an optionally substituted C3-C8 cycloalkyl, an optionally substituted phenyl, an optionally substituted aryl, or an optionally substituted heterocyclyl; and Q is a pyrrole, pyrazole, imidazole, thiazole, pyrrolidine, indole, benzofuran, 4,5,6,7-tetrahydrobenzothiophene, thieno[3,2-b]pyrrole, furo[3,2-b]pyrrole, thieno[2,3-b]pyrrole, benzimidazole, pyridine, quinoline, or 1,2,3,4-tetrahydroisoquinoline cyclic compound.

  本发明涉及新型的环化碳酰胺-氮杂杂环化合物，这些化合物是潜在的生理活性化合物（激动剂、拮抗剂和受体调节剂、酶抑制剂、抗肿瘤剂、抗菌和抗寄生虫剂等），还涉及一种包括环化碳酰胺-氮杂杂环化合物的焦点库、一种包括环化碳酰胺-氮杂杂环化合物作为活性成分的制药组合物，以及制备和使用这些化合物的方法。本发明涉及一般式1的环化碳酰胺-氮杂杂环化合物：其中：W是6-氧代哌嗪、[1,4]二氮杂环、[1,4]硫杂环或[1,4]噁唑杂环化合物，环化到至少一个可选取代和可选缩合的杂环化合物Q；R1、R2和R3独立地是氢原子、惰性取代基、可选取代的C1-C6烷基、可选取代的C3-C8环烷基、可选取代的苯基、可选取代的芳基或可选取代的杂环基；Q是吡咯、吡唑、咪唑、噻唑、吡咯烷、吲哚、苯并呋喃、4,5,6,7-四氢苯并噻吩、噻吩[3,2-b]吡咯、呋吒[3,2-b]吡咯、噻吩[2,3-b]吡咯、苯并咪唑、吡啶、喹啉或1,2,3,4-四氢异喹啉环化合物。
• ——
  作者：Thomas Lindel、Holger Hoffmann、Matthias Hochgürtel、Joseph R. Pawlik

  DOI：10.1023/a:1005591826613

  日期：——

  We investigated the relationship between the structures of pyrrole-containing alkaloids from marine sponges of the genus Agelas and their capacity to deter feeding by the omnivorous Caribbean reef fish, Thalassoma bifasciatum. Seven natural products were assayed at volumetric concentrations of 1, 5, and 10 mg/ml: dispacamide A, keramadine, oroidin, midpacamide, 4,5-dibromopyrrole-2-carboxylic acid, 4,5-dibromopyrrole-2-carboxamide, and racemic longamide A. We also assayed 14 structural analogs obtained mostly by chemical synthesis. Of the seven natural products, only rac-longamide A was not significantly deterrent at any of the assay concentrations. The pyrrole moiety was required for feeding inhibition activity, while the addition of the imidazole group enhanced this activity. Variously functionalized imidazoles lacking the pyrrole moiety were not deterrent. Combinations of the natural products appeared to have an additive effect on feeding inhibition; there was no evidence of synergy. Given their high concentrations in sponge tissue, dispacamide A and oroidin most probably serve as the primary chemical defenses of many Agelas sp., while minor compounds such as keramadine are not present in high enough concentrations to contribute much to chemical defense.
• Controlling cyclizations of 2-pyrrolecarboxamidoacetals. Facile solvation of β-amido aldehydes and revised structure of synthetic homolongamide
  作者：Ana Carolina Barrios Sosa、Kenichi Yakushijin、David A Horne

  DOI：10.1016/s0040-4039(00)00630-4

  日期：2000.6