(+/-)-longamide B | 200264-70-6

• 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: (+/-)-longamide B
• 英文别名: longamide B；2-(6,7-dibromo-1-oxo-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-4-yl)acetic acid
• CAS: 200264-70-6
• 化学式: C₉H₈Br₂N₂O₃
• 分子量: 351.982
• InChiKey: DRDCMECERMJRNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-longamide B 在 氯化亚砜 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 10.33h， 生成 2-Amino-5-(6,7-dibromo-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]pyrazin-4-ylmethyl)-imidazole-1-carboxylic acid tert-butyl ester
  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
• 作为产物：
  描述：

  2-(pyrrol-1-yl)succinic acid dimethyl ester 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 2,6-二叔丁基-4-甲基吡啶 、 10% Pt/activated carbon 、 氢气 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 44.33h， 生成 (+/-)-longamide B
  参考文献：
  名称：

  长酰胺B，长酰胺B甲酯，hanishin及其类似物的总合成和细胞毒活性。

  摘要：

  海洋生物碱，长酰胺B（1），长酰胺B甲酯（2），haishin（3）和一系列非天然存在的类似物是从廉价的市售dl-天冬氨酸二甲基酯中高效合成的。评价了这些天然产物（1-3）及其类似物（9-15）对人肺腺癌（A549）和人前列腺癌（PC3）细胞的细胞毒性。这是对这些生物碱在这些癌细胞系中的细胞毒性的首次评估，结果表明类似物15具有与其天然母体化合物（±）-hanishin（3）相当的细胞毒性活性。该研究为进一步开发这些生物碱进行结构修饰提供有用的信息，以开发新型抗肿瘤药。

  DOI：

  10.1016/j.bmcl.2015.11.069

文献信息

• 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。
• Syntheses and Preliminary Biological Evaluations of the Dibromopyrrole‐Containing Marine Natural Products Agesasine A, Agesasine B, Longamide E and Various Congeners
  作者：Chengzhi Chen、Tingting Yuan、Ping Lan、Lorenzo V. White、Jing Chen、Martin Banwell

  DOI：10.1002/ejoc.202300003

  日期：——

  synthesis of various, recently reported, marine-derived, pyrrole-containing natural products are reported. The evaluation of these and certain congeners, some of which were prepared by potentially biomimetic means, against a panel of four human-cancer cell lines reveals significant variations in activity as a function of structure.

  报道了最近报道的各种海洋衍生的含吡咯天然产物的合成。这些和某些同类物（其中一些是通过潜在的仿生手段制备的）针对一组四种人类癌细胞系的评估揭示了作为结构函数的活性的显着变化。
• Total synthesis of rac-longamide B
  作者：Xue-Tong Sun、Austin Chen

  DOI：10.1016/j.tetlet.2007.03.022

  日期：2007.5

  rac-Longamide B has been synthesized in six-steps from known starting materials. The synthesis is highlighted by a novel palladium-catalyzed double allylic alkylation of amidopyrroles with 2-butene-1,4-di-tert-butyl dicarbonate. (c) 2007 Elsevier Ltd. All rights reserved.
• Annellated carbamyl-aza-heterocyclic compounds, a focused library, pharmaceutical compositions, and methods of preparing the same
  申请人：Ivashchenko Alexander

  公开号：US20070191337A1

  公开（公告）日：2007-08-16

  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; R 1 , R 2 and R 3 are, independently of one another, a hydrogen atom, an inert substituent, an optionally substituted C 1 -C 6 alkyl, an optionally substituted C 3 -C 8 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.
• [EN] AZAHETEROCYCLES, COMBINATORY LIBRARY, FOCUSED LIBRARY, PHARMACEUTICAL COMPOSITION AND METHODS FOR THE PRODUCTION THEREOF<br/>[FR] BIBLIOTHÈQUES COMBINATOIRE ET FOCALISÉE D'AZAHÉTÉROCYCLES, COMPOSITION PHARMACEUTIQUE ET PROCÉDÉS DE LEUR FABRICATION
  申请人：CHEMICAL DIVERSITY RES INST LT

  公开号：WO2007117180A1

  公开（公告）日：2007-10-18

  [EN] The invention relates to novel azaheterocycles of interest as potential physiologically active substances (agonists, antagonists, receptor modulators, ferment inhibitors, oncolytics, antibacterial and antiparasitic agent etc.), to combinatory and focused libraries comprising novel azaheterocycles of a pharmaceutical composition containing said novel azaheterocycles in the form of an active substance and to methods for the production and the use thereof. Said novel azaheterocycles are of general formula (1), wherein W is an azaheterocycle which comprises 6-12 atoms, is optionally annelated, has at least one C₅-C₇ carbocycle and/or heterocycle, and also comprises at least one of heteroatoms and is selected from an O, S or N group; R₁
  [FR] L'invention concerne de nouveaux azahétérocycles qui représentent un intérêt certain en tant que substances physiologiquement actives potentielles (agonistes, antagonistes et modulateurs de récepteurs, inhibiteurs de ferments, oncolytiques, antibactériens, antiparasitaires, etc.), des bibliothèques combinatoire et focalisée comprenant de nouveaux azahétérocycles, une composition pharmaceutique contenant en tant que substance active de nouveaux azahétérocycles, leurs procédés de fabrication et d'utilisation. L'invention porte sur de nouveaux azahétérocycles ayant la formule générale (1), dans laquelle W est un hétérocycle comprenant de 6 à 12 atomes éventuellement hybridé à un carbocycle et/ou hétérocycle C₅-C₇, qui comprend au moins un hétéro-atome sélectionné dans le groupe O, S ou N, R₁