5-aminopentyl-5-[(1H-indol-3-yl)methyl]-1,2,4-oxadiazol-3-amine | 1374238-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-aminopentyl-5-[(1H-indol-3-yl)methyl]-1,2,4-oxadiazol-3-amine
• 英文别名: N'-[5-(1H-indol-3-ylmethyl)-1,2,4-oxadiazol-3-yl]pentane-1,5-diamine
• CAS: 1374238-53-5
• 化学式: C₁₆H₂₁N₅O
• 分子量: 299.376
• InChiKey: CSIDNHPHLNYWKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-aminopentyl-5-[(1H-indol-3-yl)methyl]-1,2,4-oxadiazol-3-amine 在 silver nitrate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 phidianidine B trifluoroacetate salt
  参考文献：
  名称：

  Synthesis of Phidianidines A and B

  摘要：

  Reaction of a substituted indole-3-acetyl chloride with N-5-azidopentyl-N'-hydroxyguanidine generated a substituted 3-(5-azidopentylamino)-5-((indol-3-yl)methyl)-1,2,4-oxadiazole. Reduction of the azide with zinc and ammonium formate afforded the amine, which was elaborated to the guanidine, completing short and efficient syntheses of the cytotoxic natural products phidianidines A and B in 19% overall yield by a convergent route that will make analogues readily available for biological evaluation. Initial screening in the NCI 60 cell line at 10(-5) M indicated that the bromine on the indole is necessary for activity and that the amine precursor to phidianidine A is more potent than phidianidine A.

  DOI：

  10.1021/jo300449n
• 作为产物：
  描述：

  5-(T-boc-氨基)-1-戊基溴 在 盐酸羟胺 、 sodium methylate 、 sodium hydride 、 sodium amide 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 22.17h， 生成 5-aminopentyl-5-[(1H-indol-3-yl)methyl]-1,2,4-oxadiazol-3-amine
  参考文献：
  名称：

  Phidianidine B 的合成，一种高细胞毒性的 1,2,4-恶二唑海洋代谢物

  摘要：

  Phidianidine B (1) 是一种天然 1,2,4-恶二唑，可连接吲哚系统和最近从海洋软体动物中报道的氨基烷基胍基团，分七步合成（总产率 14%）。该合成程序基于 3 吲哚乙酸甲酯和氨基-烷基羟基胍中间体 2 的偶合，适时制备，具有普遍应用性，可以合成具有不同烷基链长度或吲哚环取代的类似物.

  DOI：

  10.3998/ark.5550190.0013.919

文献信息

• NEW 1,2,4-OXADIAZOL DERIVATIVES, PROCESS FOR THEIR PREPARATION AND USE THEREOF AS INTERMEDIATES IN THE PREPARATION OF INDOLIC ALKALOIDS
  申请人：CONSIGLIO NAZIONALE DELLE RICERCHE

  公开号：US20150051405A1

  公开（公告）日：2015-02-19

  The present invention relates in general terms to a variously substituted 1,2,4-oxadiazol derivative, a process for their preparation, and use thereof as an intermediate in the preparation of indolic alkaloids, including phidianidine B and A.

  本发明涉及一种各种取代的1,2,4-噁二唑衍生物，其制备方法以及将其用作吲哚生物碱制备中间体的用途。
• [EN] NEW 1, 2, 4-OXADIAZOL DERIVATIVES, PROCESS FOR THEIR PREPARATION AND USE THEREOF AS INTERMEDIATES IN THE PREPARATION OF INDOLIC ALKALOIDS<br/>[FR] NOUVEAUX DÉRIVÉS DE 1,2,4-OXADIAZOLE, LEUR PROCÉDÉ DE PRÉPARATION ET UTILISATION DE CEUX-CI COMME INTERMÉDIAIRES DANS LA PRÉPARATION D'ALCALOÏDES INDOLIQUES
  申请人：CONSIGLIO NAZIONALE RICERCHE

  公开号：WO2013140331A1

  公开（公告）日：2013-09-26

  The present invention relates in general terms to a variously substituted 1, 2, 4-oxadiazol derivative, a process for their preparation, and use thereof as an intermediate in the preparation of indolic alkaloids, including phidianidine B and A.

  本发明一般涉及各种取代的1,2,4-噁二唑衍生物，其制备方法以及将其用作吲哚生物碱制备中间体，包括phidianidine B和A的用途。
• Design and Synthesis of Marine Phidianidine Derivatives as Potential Immunosuppressive Agents
  作者：Jin Liu、Heng Li、Kai-Xian Chen、Jian-Ping Zuo、Yue-Wei Guo、Wei Tang、Xu-Wen Li

  DOI：10.1021/acs.jmedchem.8b01430

  日期：2018.12.27

  A series of novel marine phidianidine derivatives were designed, synthesized, and evaluated for their immunosuppressive activities during our search of potential immunosuppressive agents with high efficacy and low toxicity from marine sources. These compounds were tested for their inhibitory activity on Con A-induced T cell and lipopolysaccharide-induced B cell proliferation. Compounds 14a and 18c

  在我们寻找海洋来源的高效，低毒的潜在免疫抑制剂过程中，设计，合成了一系列新型海洋phidianidine衍生物，并对其免疫抑制活性进行了评估。测试了这些化合物对Con A诱导的T细胞和脂多糖诱导的B细胞增殖的抑制活性。化合物14a和18c表现出最有希望的抑制作用和低毒性，被发现分别在纯化的T细胞和B细胞上交联T细胞受体（TCR）和B细胞受体（BCR）后具有免疫调节活性。 。
• US9085569B2
  申请人：——

  公开号：US9085569B2

  公开（公告）日：2015-07-21
• Synthesis of Phidianidine B, a highly cytotoxic 1,2,4-oxadiazole marine metabolite
  作者：Emiliano Manzo、Dario Pagano、Marianna Carbone、M. Letizia Ciavatta、Margherita Gavagnin

  DOI：10.3998/ark.5550190.0013.919

  日期：——

  Phidianidine B (1), a natural 1,2,4-oxadiazole linking both an indole system and an aminoalkyl guanidine group that has been recently reported from a marine mollusk, has been synthesized in seven steps (14% total yield). The synthetic procedure, which is based on the coupling of 3indolacetic acid methyl ester and the amino-alkyl hydroxy guanidine intermediate 2, opportunely prepared, is of general

  Phidianidine B (1) 是一种天然 1,2,4-恶二唑，可连接吲哚系统和最近从海洋软体动物中报道的氨基烷基胍基团，分七步合成（总产率 14%）。该合成程序基于 3 吲哚乙酸甲酯和氨基-烷基羟基胍中间体 2 的偶合，适时制备，具有普遍应用性，可以合成具有不同烷基链长度或吲哚环取代的类似物.