2,4,5,6-tetraaminoquinazoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,4,5,6-tetraaminoquinazoline
• 英文别名: quinazoline-2,4,5,6-tetraamine；Quinazoline-2,4,5,6-tetramine
• 化学式: C₈H₁₀N₆
• 分子量: 190.208
• InChiKey: QTMJIODDNNBRTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4,5,6-tetraaminoquinazoline 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 2,4,5,6-tetraaminoquinazoline dihydrochloride
  参考文献：
  名称：

  Fragment based search for small molecule inhibitors of HIV-1 Tat-TAR

  摘要：

  Basic molecular building blocks such as benzene rings, amidines, guanidines, and amino groups have been combined in a systematic way to generate ligand candidates for HIV-1 TAR RNA. Ranking of the resulting compounds was achieved in a fluorimetric Tat-TAR competition assay. Although simple molecules such as phenylguanidine are inactive, few iteration steps led to a set of ligands with IC50 values ranging from 40 to 150 mu M. 1,7-Diaminoisoquinoline 17 and 2,4,6-triaminoquinazoline 22 have been further characterized by NMR titrations with TAR RNA. Compound 22 is bound to TAR at two high affinity sites and shows slow exchange between the free ligand and the RNA complex. These results encourage investigations of dimeric ligands built from two copies of compound 22 or related heterocycles. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.004
• 作为产物：
  描述：

  7,9-diamino-[1,2,5]oxadiazolo[3,4-f]quinazoline-3-oxide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 2,4,5,6-tetraaminoquinazoline
  参考文献：
  名称：

  Fragment based search for small molecule inhibitors of HIV-1 Tat-TAR

  摘要：

  Basic molecular building blocks such as benzene rings, amidines, guanidines, and amino groups have been combined in a systematic way to generate ligand candidates for HIV-1 TAR RNA. Ranking of the resulting compounds was achieved in a fluorimetric Tat-TAR competition assay. Although simple molecules such as phenylguanidine are inactive, few iteration steps led to a set of ligands with IC50 values ranging from 40 to 150 mu M. 1,7-Diaminoisoquinoline 17 and 2,4,6-triaminoquinazoline 22 have been further characterized by NMR titrations with TAR RNA. Compound 22 is bound to TAR at two high affinity sites and shows slow exchange between the free ligand and the RNA complex. These results encourage investigations of dimeric ligands built from two copies of compound 22 or related heterocycles. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.004

文献信息

• [EN] DRUG-LIKE MOLECULES AND METHODS FOR THE THERAPEUTIC TARGETING OF VIRAL RNA STRUCTURES<br/>[FR] MOLÉCULES DE TYPE MÉDICAMENT ET MÉTHODES POUR LE CIBLAGE THÉRAPEUTIQUE DE STRUCTURES D'ARN VIRAL
  申请人：UNIV WASHINGTON

  公开号：WO2021242770A1

  公开（公告）日：2021-12-02

  Methods for identifying selective RNA-binding small molecules by NMR screening. The method provides a screening cascade to identify molecules that bind to an RNA structure, such as HIV TAR. Compounds that bind to structured RNAs and that are useful to disrupt the formation of RNA-protein complexes, such as P-TEFb-Tat-TAR complex.

  通过NMR筛选识别选择性RNA结合小分子的方法。该方法提供了一个筛选级联，以识别与RNA结构（如HIV TAR）结合的分子。这些结合到结构化RNA并有助于破坏RNA-蛋白质复合物形成的化合物，如P-TEFb-Tat-TAR复合物。
• [EN] SMALL MOLECULE INTERVENTION IN HIV-1 REPLICATION<br/>[FR] INTERVENTION DE PETITES MOLECULES DANS LA REPLICATION DU VIH-1
  申请人：——

  公开号：WO1999025327A2

  公开（公告）日：1999-05-27

  [EN] The instant invention is a series of small molecules which are inhibitors of HIV-1 Tat-TAR interaction. The compounds are useful in the treatment of HIV-1 infections.
  [FR] La présente invention est une série de petites molécules lesquelles sont des inhibiteurs de l'interaction Tat-TAR du VIH-1. Les composés sont utiles dans le traitement d'infections à VIH-1.
• Fragment based search for small molecule inhibitors of HIV-1 Tat-TAR
  作者：Mirco Zeiger、Sebastian Stark、Elisabeth Kalden、Bettina Ackermann、Jan Ferner、Ute Scheffer、Fatemeh Shoja-Bazargani、Veysel Erdel、Harald Schwalbe、Michael W. Göbel

  DOI：10.1016/j.bmcl.2014.11.004

  日期：2014.12

  Basic molecular building blocks such as benzene rings, amidines, guanidines, and amino groups have been combined in a systematic way to generate ligand candidates for HIV-1 TAR RNA. Ranking of the resulting compounds was achieved in a fluorimetric Tat-TAR competition assay. Although simple molecules such as phenylguanidine are inactive, few iteration steps led to a set of ligands with IC50 values ranging from 40 to 150 mu M. 1,7-Diaminoisoquinoline 17 and 2,4,6-triaminoquinazoline 22 have been further characterized by NMR titrations with TAR RNA. Compound 22 is bound to TAR at two high affinity sites and shows slow exchange between the free ligand and the RNA complex. These results encourage investigations of dimeric ligands built from two copies of compound 22 or related heterocycles. (C) 2014 Elsevier Ltd. All rights reserved.