2-氨基组胺 | 39050-13-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-氨基组胺
• 中文别名: 4-(2-氨基乙基)-3H-咪唑-2-胺；2-氨基-1H-咪唑-5-乙胺
• 英文名称: 2-(2-amino-4-imidazolil)etilammina
• 英文别名: 2-aminohistamine；5-(2-aminoethyl)-1H-imidazol-2-amine
• CAS: 39050-13-0
• 化学式: C₅H₁₀N₄
• mdl: MFCD08668294
• 分子量: 126.161
• InChiKey: PDWGQCUSLDPUFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  80.7
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  2-氨基组胺 在 四氯苯醌 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Concise Total Synthesis of the Marine Natural Product Ageladine A

  摘要：

  A total synthesis of ageladine A has been achieved by exploiting a Pictet-Spengler- type condensation between 2-aminohistamine and 4,5dibromo-2-formylpyrrole as the key step.

  DOI：

  10.1021/ol061584y
• 作为产物：
  描述：

  N-{2-[2-(4-bromo-phenylazo)-3H-imidazol-4-yl]-ethyl}-acetamide 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、241.32 kPa 条件下， 生成 2-氨基组胺
  参考文献：
  名称：

  含新型P1针作为TF / VIIa抑制剂的吡嗪酮的设计，合成和生物学评估。

  摘要：

  本文描述了一系列取代的吡嗪酮作为TF / VIIa复合物抑制剂的设计，合成和酶促活性。设计这些抑制剂以探索先前描述的P1 idine的置换和变异[J. 中 Chem.2003，46，4050]。根据与母体苯基am（pKa约为12）相比降低的碱性，选择P1针头替代品。影响化合物口服生物利用度的一个因素是该化合物在肠道中的电离状态。该研究的理想结果是确定一种口服生物利用的TF-VIIa抑制剂。

  DOI：

  10.1016/j.bmcl.2007.05.090

文献信息

• [EN] SYNTHESIS OF AGELADINE A AND ANALOGS THEREOF<br/>[FR] SYNTHÈSE D'AGÉLADINE A ET D'ANALOGUES DE CELLE-CI
  申请人：UNIV MACQUARIE

  公开号：WO2009152584A1

  公开（公告）日：2009-12-23

  The invention describes a one pot process for synthesizing a compound of structure (I), or a tautomer thereof. A compound of structure (II), or a tautomer thereof, and an aldehyde of structure RdCHO are condensed to form a condensation product. The resulting condensation product is then oxidized in the same reaction mixture to produce the compound of structure (I) or a tautomer thereof.

  该发明描述了一种一锅法合成结构式(I)化合物或其同分异构体的过程。将结构式(II)化合物或其同分异构体与RdCHO结构的醛缩合形成缩合产物。然后将所得缩合产物在同一反应混合物中氧化，以产生结构式(I)化合物或其同分异构体。
• [EN] AMINO-HETEROARYL-CONTAINING PROKINETICIN 1 RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DE RÉCEPTEUR DE LA PROKINÉTICINE 1 À TENEUR EN AMINO-HÉTÉROARYLE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2009058653A1

  公开（公告）日：2009-05-07

  The present invention relates to certain novel compounds of Formula (I): and methods for preparing these compounds, compositions, intermediates and derivatives thereof and for the treatment of prokineticin 1 or prokinetin 1 receptor mediated disorders.

  本发明涉及某些新型化合物的公式（I）以及制备这些化合物、组合物、中间体和衍生物的方法，用于治疗促动素1或促动素1受体介导的疾病。
• Synthesis and anticancer activities of ageladine A and structural analogs
  作者：Yuelong Ma、Sangkil Nam、Richard Jove、Kenichi Yakushijin、David A. Horne

  DOI：10.1016/j.bmcl.2009.11.036

  日期：2010.1

  ageladine A analogs that include 2-aminoimidazo[4,5-c]azepines (seven-membered rings) and 2-amino-3H-imidazo[4,5-c]pyridine (six-membered rings) derivatives were synthesized and evaluated for their anticancer effects against several human cancer cell lines and MMP-2 inhibition in vitro. Only compounds possessing the aromatic azepine (seven-membered ring) core showed anticancer activity with IC50 values

  一系列ageladine A类似物的包括2-氨基咪唑并[4,5- Ç ]氮杂（七元环）和2-氨基-3- ħ -咪唑并[4,5- Ç ]吡啶（六元环）衍生物是合成并评估了它们对几种人类癌细胞系的抗癌作用和体外 MMP-2 抑制作用。只有具有芳香氮杂（七元环）核心的化合物显示出抗癌活性，IC 50值在低微摩尔范围内。
• A One-Pot Synthesis and Biological Activity of Ageladine A and Analogues
  作者：Sudhir R. Shengule、Wendy L. Loa-Kum-Cheung、Christopher R. Parish、Mélina Blairvacq、Laurent Meijer、Yoichi Nakao、Peter Karuso

  DOI：10.1021/jm200039m

  日期：2011.4.14

  A one-pot synthesis of ageladine A and analogues is reported. The key Pictet - Spengler reaction between 2-aminohistamine and aryl aldehydes has been successfully utilized for the synthesis of the natural product and 14 analogues. These compounds were screened for their matrix metalloprotease (MMP) and kinase inhibition to develop the first structure-activity relationship of ageladine A analogues. One compound, which showed significant kinase activity but little MMP inhibitory activity, was found to be highly active in an antiangiogenic screen, suggesting that the angiogenic activity of ageladine A is not associated with MMP inhibition but rather kinase inhibitory activity. Cytotoxicity was excluded as a mode of action by the assay of ageladine A and an analogue against 60 human cell lines.
• Synthesis and Biological Evaluation of Purealin and Analogues as Cytoplasmic Dynein Heavy Chain Inhibitors
  作者：Guangyu Zhu、Fanglong Yang、Raghavan Balachandran、Peter Höök、Richard B. Vallee、Dennis P. Curran、Billy W. Day

  DOI：10.1021/jm051030l

  日期：2006.3.1

  Cytoplasmic dynein plays important roles in membrane transport, mitosis, and other cellular processes. A few small-molecule inhibitors of cytoplasmic dynein have been identified. We report here the first synthesis of purealin, a natural product isolated from the sea sponge Psammaplysilla purea, which is known to inhibit axonemal dynein. Also described are the first syntheses, by modular amide coupling reactions, of the natural product purealidin A (a component of purealin) and a small library of analogues. The library was examined for inhibition of cytoplasmic dynein heavy chain and cell growth. The compounds showed effective antiproliferative activity against a mouse leukemia cell line but selective activities against human carcinoma cell lines. Purealin and some of the analogues inhibited the microtubule-stimulated ATPase activity of recombinant cytoplasmic dynein heavy chain motor domain. The inhibitory effect of purealin was concentration dependent and uncompetitive, supporting the hypothesis that it does not compete with the binding of ATP.