5-溴-6-氨基尿嘧啶 | 6312-73-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 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: 5-溴-6-氨基尿嘧啶
• 英文名称: 6-amino-5-bromo-2,4(1H,3H)-pyrimidinedione
• 英文别名: 5-bromo-6-aminouracil；6-amino-5-bromouracil；6A5BU；6-amino-5-bromo-1H-pyrimidine-2,4-dione；6-Amino-5-brom-1H-pyrimidin-2,4-dion；6-amino-5-bromopyrimidine-2,4(1H,3H)-dione；6-amino-5-bromo-1H-pyrimidine-2,4-dione
• CAS: 6312-73-8
• 化学式: C₄H₄BrN₃O₂
• mdl: MFCD00830386
• 分子量: 205.999
• InChiKey: FSLBEEVCUZFKRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.2
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  5-溴-6-氨基尿嘧啶 在 sodium disulfide 、 乙醇 作用下， 生成 6,6'-diamino-1H,1'H-5,5'-disulfanediyl-bis-pyrimidine-2,4-dione
  参考文献：
  名称：

  193.嘧啶-5-基硫化物和二硫化物的合成。第二部分

  摘要：

  DOI：

  10.1039/jr9560000917
• 作为产物：
  描述：

  4-氨基-2,6-二羟基嘧啶 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-溴-6-氨基尿嘧啶
  参考文献：
  名称：

  用于设计氮杂环作为结核分枝杆菌二氢叶酸还原酶抑制剂的片段发现

  摘要：

  基于片段的药物设计用于鉴定结核分枝杆菌 (Mtb) 二氢叶酸还原酶 (DHFR) 抑制剂。针对 Mtb DHFR 酶的配体筛选导致鉴定出多个片段命中，IC50 值在 38-90 μM 范围内，而最小抑制浓度 (MIC) 值在 31.5-125 μg/mL 范围内。这些片段支架可用于抗结核药物设计。

  DOI：

  10.1002/ardp.201600066

文献信息

• Substituted 5-phenylthio-6-amino-pyrimidinones, a process for their
  申请人：Beiersdorf Aktiengesellschaft

  公开号：US04594419A1

  公开（公告）日：1986-06-10

  Substituted 5-phenylthio-6-aminopyrimidinones of the general formula I ##STR1## in which R denotes an amino or hydroxyl group, and their tautomeric forms and acid addition salts thereof, have diuretic, saluretic and uricosuric actions. They can be used as medicaments for the treatment of hypertension, hyperuricemia and edemas.

  通式为I的5-苯硫基-6-氨基嘧啶酮被替代，其中R表示氨基或羟基，它们的互变异构体和酸加成盐具有利尿、盐利和尿酸排泄作用。它们可用作治疗高血压、高尿酸血症和水肿的药物。
• 5-halo-6-amino-uracils and derivatives thereof
  申请人：SEARLE &

  公开号：US02731465A1

  公开（公告）日：1956-01-17
• Barker et al., Journal of the Chemical Society, 1954, p. 4206,4209
  作者：Barker et al.

  DOI：——

  日期：——
• Xanthine oxidase-activated prodrugs of thymidine phosphorylase inhibitors
  作者：Philip Reigan、Abdul Gbaj、Ian J. Stratford、Richard A. Bryce、Sally Freeman

  DOI：10.1016/j.ejmech.2007.07.015

  日期：2008.6

  Thymidine phosphorylase (TP) is over-expressed in various tumour types and plays an important role in tumour angiogenesis, growth, invasion and metastasis. The enzymatic activity of TP is required for the angiogenic effect of TP, therefore, inhibitors of TP are of significant interest in cancer chemotherapy. A series of xanthine oxidase (XO) activated prodrugs of known inhibitors of TP have been designed and synthesized with the ultimate intent of improving tumour selectivity and pharmacokinetic characteristics. These prodrugs were not inhibitors of TP, but were selectively oxidized by XO at C-2 and/or C-4 of the uracil ring moiety to generate the desired TP inhibitor. Molecular modelling of both the TP inhibitors and XO-activated prodrugs rationalized their binding in the active site of the human TP crystal structure. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Synthesis and enzymatic evaluation of xanthine oxidase-activated prodrugs based on inhibitors of thymidine phosphorylase
  作者：Philip Reigan、Abdul Gbaj、Edwin Chinje、Ian J. Stratford、Kenneth T. Douglas、Sally Freeman

  DOI：10.1016/j.bmcl.2004.08.036

  日期：2004.11

  A series of xanthine oxidase-activated prodrugs of known inhibitors of thymidine phosphorylase has been designed and synthesised to introduce turnout selectivity. These prodrugs were oxidised by xanthine oxidase at C-2 and/or C-4 of the uracil ring to generate the desired TP inhibitor. (C) 2004 Elsevier Ltd. All rights reserved.