3-(4-溴丁基)-1,6-二甲基嘧啶-2,4-二酮 | 63594-12-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 3-(4-溴丁基)-1,6-二甲基嘧啶-2,4-二酮
• 英文名称: 3-(4-bromo-butyl)-1,6-dimethyl-1H-pyrimidine-2,4-dione
• 英文别名: 3-(4-bromobutyl)-1,6-dimethylpyrimidine-2,4(1H,3H)-dione；3-(4-bromobutyl)-1,6-dimethylpyrimidine-2,4-dione
• CAS: 63594-12-7
• 化学式: C₁₀H₁₅BrN₂O₂
• 分子量: 275.145
• InChiKey: NJAHBBATUVQKDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-溴丁基)-1,6-二甲基嘧啶-2,4-二酮 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 32.0h， 生成 bis[4-(3,6-dimethyluracil-1-yl)butyl]benzylethylammonium bromide
  参考文献：
  名称：

  Antibacterial and antifungal activity of acyclic and macrocyclic uracil derivatives with quaternized nitrogen atoms in spacers

  摘要：

  The reactions of 1,3-bis(alpha,omega-bromoalkyl)-6-methyluracils with 1,3-bis(alpha,omega-ethylaminoalkyl)-6-methyluracils or 1,3-bis(bromopentyl)thymine with butylamine afforded pyrimidinophanes containing one or two uracil units and nitrogen atoms in bridging polymethylene chains. In some cases individual geometric isomers of pyrimidinophanes differing in the mutual arrangement of the carbonyl and methyl groups at different pyrimidine rings were isolated. Quaternization of the bridging nitrogen atom with o-nitrobenzyl bromide, benzyl bromide, n-decyl bromide gave rise to water-soluble pyrimidinophanes which were evaluated for their antibacterial and antifungal activity. The arrangement of the carbonyl groups in macrocycles doesn't affect the activity. Antibacterial and antifungal activity of pyrimidinophanes increases with the increase of polymethylene N-(pyr)-N-chain length and dramatically increases upon the introduction of n-decyl substituent at nitrogen atoms in spacers. Pyrimidi-nophanes with 5 and 6 methylene groups in N(pyr)-N-chain and n-decyl substituent showed significant bacteriostatic, fungistatic, bactericidal, fungicidal activity which comparable with standard antibacterial and antifungal drugs. Acyclic counterpart demonstrated the highest activity against fungi. Toxicity of more effective pyrimidinophanes was determined for mice and Daphnia magna Straus. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.03.030
• 作为产物：
  描述：

  1,6-dimethylpyrimidine-2,4(1H,3H)-dione 、 1,4-二溴丁烷 以75%的产率得到
  参考文献：
  名称：

  REZNIK V. S.; SALIXOV I. SH.; SHVETSOV YU. S.; SHIRSHOV A. N.; BAKULIN V.+, IZV. AN CCCP. CEP. XIM., 1977, HO 4, 880-884

  摘要：

  DOI：

文献信息

• Second Generation Tetrahydroquinoline-Based Protein Farnesyltransferase Inhibitors as Antimalarials
  作者：Pravin Bendale、Srinivas Olepu、Praveen Kumar Suryadevara、Vivek Bulbule、Kasey Rivas、Laxman Nallan、Brian Smart、Kohei Yokoyama、Sudha Ankala、Prakash Rao Pendyala、David Floyd、Louis J. Lombardo、David K. Williams、Frederick S. Buckner、Debopam Chakrabarti、Christophe L. M. J. Verlinde、Wesley C. Van Voorhis、Michael H. Gelb

  DOI：10.1021/jm0703340

  日期：2007.9.1

  Substituted tetrahydroquinolines (THQs) have been previously identified as inhibitors of mammalian protein farnesyltransferase (PFT). Previously we showed that blocking PFT in the malaria parasite led to cell death and that THQ-based inhibitors are the most potent among several structural classes of PFT inhibitors (PFTIs). We have prepared 266 THQ-based PFTIs and discovered several compounds that inhibit the malarial enzyme in the sub- to low-nanomolar range and that block the growth of the parasite (P. falciparum) in the lownanomolar ran-e. This body of structure- activity data can be rationalized in most cases by consideration of the X-ray structure of one of the THQs bound to mammalian PFT together with a homology structural model of the malarial enzyme. The results of this study provide the basis for selection of antimalarial PFTIs for further evaluation in preclinical drug discovery assays.
• Antibacterial and antifungal activity of acyclic and macrocyclic uracil derivatives with quaternized nitrogen atoms in spacers
  作者：V.E. Semenov、A.D. Voloshina、E.M. Toroptzova、N.V. Kulik、V.V. Zobov、R.K. Giniyatullin、A.S. Mikhailov、A.E. Nikolaev、V.D. Akamsin、V.S. Reznik

  DOI：10.1016/j.ejmech.2006.03.030

  日期：2006.9

  The reactions of 1,3-bis(alpha,omega-bromoalkyl)-6-methyluracils with 1,3-bis(alpha,omega-ethylaminoalkyl)-6-methyluracils or 1,3-bis(bromopentyl)thymine with butylamine afforded pyrimidinophanes containing one or two uracil units and nitrogen atoms in bridging polymethylene chains. In some cases individual geometric isomers of pyrimidinophanes differing in the mutual arrangement of the carbonyl and methyl groups at different pyrimidine rings were isolated. Quaternization of the bridging nitrogen atom with o-nitrobenzyl bromide, benzyl bromide, n-decyl bromide gave rise to water-soluble pyrimidinophanes which were evaluated for their antibacterial and antifungal activity. The arrangement of the carbonyl groups in macrocycles doesn't affect the activity. Antibacterial and antifungal activity of pyrimidinophanes increases with the increase of polymethylene N-(pyr)-N-chain length and dramatically increases upon the introduction of n-decyl substituent at nitrogen atoms in spacers. Pyrimidi-nophanes with 5 and 6 methylene groups in N(pyr)-N-chain and n-decyl substituent showed significant bacteriostatic, fungistatic, bactericidal, fungicidal activity which comparable with standard antibacterial and antifungal drugs. Acyclic counterpart demonstrated the highest activity against fungi. Toxicity of more effective pyrimidinophanes was determined for mice and Daphnia magna Straus. (c) 2006 Elsevier SAS. All rights reserved.
• REZNIK V. S.; SALIXOV I. SH.; SHVETSOV YU. S.; SHIRSHOV A. N.; BAKULIN V.+, IZV. AN CCCP. CEP. XIM., 1977, HO 4, 880-884
  作者：REZNIK V. S.、 SALIXOV I. SH.、 SHVETSOV YU. S.、 SHIRSHOV A. N.、 BAKULIN V.+

  DOI：——

  日期：——