2,4-diamino-6-methylquinazoline | 1955-61-9

• 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-diamino-6-methylquinazoline
• 英文别名: 6-methyl-2,4-diaminoquinazoline；6-methyl-2,4-quinazolinediamine；6-methyl-quinazoline-2,4-diamine；2,4-Diamino-6-methyl-chinazolin；6-methylquinazoline-2,4-diamine
• CAS: 1955-61-9
• 化学式: C₉H₁₀N₄
• 分子量: 174.205
• InChiKey: LSNYLNXZYSKOGM-UHFFFAOYSA-N

物化性质

• 熔点：
  258-259.5 °C
• 沸点：
  461.2±37.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2,4-diamino-6-methylquinazoline 在 盐酸 、 potassium phosphate 、 N-溴代丁二酰亚胺(NBS) 、 三乙胺 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 四氯化碳 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (2,4-diaminoquinazolin-6-yl)methyl 4-(4-fluorophenyl)piperazine-1-carbodithioate
  参考文献：
  名称：

  Synthesis and antiproliferative activity of 4-substituted-piperazine-1-carbodithioate derivatives of 2,4-diaminoquinazoline

  摘要：

  A novel series of 4-substituted-piperazine-1-carbodithioate derivatives of 2,4-diaminoquinazoline were synthesized and tested for their antiproliferative activities against five human cancer cell lines including A549 (lung cancer), MCF-7 (breast adenocarcinoma), HeLa (cervical carcinoma), HT29 and HCT-116 (colorectal cancer). Most of the synthesized compounds showed broad spectrum antiproliferative activity (IC50 1.47-11.83 mu M), of which 8f, 8m and 8q were the most active members with IC50 values in the range of 1.58-2.27, 1.84-3.27 and 1.47-4.68 mu M against five cancer cell lines examined, respectively. Further investigations revealed that compounds 8f, 8m and 8q exhibited weak inhibition against dihydrofolate reductase and no activity against thymidylate synthase, while induced DNA damage and activated the G2/M checkpoint in HCT-116 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.017
• 作为产物：
  描述：

  3-氯-4-硝基甲苯 在 盐酸 、 tin(ll) chloride 作用下， 以 various solvent(s) 为溶剂， 反应 8.75h， 生成 2,4-diamino-6-methylquinazoline
  参考文献：
  名称：

  一系列2,4-二氨基-6-[（N-烷基苯胺基）甲基]喹唑啉的合成及其抗疟活性†

  摘要：

  通过将2，4-二苯甲酰氨基-6-甲基喹唑啉溴化，然后用仲芳基胺处理并用碱解封，制备了一系列2，4-二氨基-6-[（N-烷基苯胺基）甲基]喹唑啉。多种类似物显示出了对小鼠伯氏疟原虫感染的显着活性。

  DOI：

  10.1002/jhet.5570240210

文献信息

• Process for synthesizing antifolates
  申请人：——

  公开号：US20040092739A1

  公开（公告）日：2004-05-13

  This invention relates to a process for synthesizing certain folic acid analogues, which are useful in treating cancer, inflammatory diseases, autoimmune diseases, and are commonly referred to as antifolates. The process employs improved steps for annulation, derivatization and addition reactions to produce the described antifolates from commonly available starting materials.

  这项发明涉及一种合成特定叶酸类似物的过程，这些类似物在治疗癌症、炎症性疾病、自身免疫性疾病中很有用，通常被称为抗叶酸类药物。该过程利用改进的环化、衍生化和加成反应步骤，从常见的起始原料中生产所述的抗叶酸类药物。
• 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.
• Efficient Copper-Catalyzed Synthesis of 4-Aminoquinazoline and 2,4-Diaminoquinazoline Derivatives
  作者：Hua Fu、Renzhong Qiao、Xiaobo Yang、Hongxia Liu、Yuyang Jiang、Yufen Zhao

  DOI：10.1055/s-0029-1218530

  日期：2010.1

  We have developed an efficient copper-catalyzed method for the synthesis of 4-aminoquinazoline and 2,4-diaminoquinazoline derivatives via reactions of substituted 2-bromobenzonitriles with amidines or guanidine, and the method is of economical and practical advantage.
• WERBEL L. M.; ELSLAGER E. F.; NEWTON L. S., J. HETEROCYCL. CHEM., 24,(1987) N 2, 345-349
  作者：WERBEL L. M.、 ELSLAGER E. F.、 NEWTON L. S.

  DOI：——

  日期：——
• METABOLICALLY INERT ANTI-INFLAMMATORY AND ANTI-TUMOR ANTIFOLATES
  申请人：NAIR, Madhavan G.

  公开号：EP1062209B1

  公开（公告）日：2009-05-13