4-溴-2,6-双(苯基甲氧基)嘧啶 | 70523-27-2

• 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: 4-溴-2,6-双(苯基甲氧基)嘧啶
• 英文名称: 6-bromo-2,4-bis(benzyloxy)pyrimidine
• 英文别名: 2,4-bis(benzyloxy)-6-bromopyrimidine；4-bromo-2,6-bis(phenylmethoxy)pyrimidine
• CAS: 70523-27-2
• 化学式: C₁₈H₁₅BrN₂O₂
• 分子量: 371.233
• InChiKey: JVMANPYCAJCWPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-溴-2,6-双(苯基甲氧基)嘧啶 在 sodium tetrahydroborate 、 正丁基锂 、 乙酸酐 、 cesium fluoride 作用下， 以 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.16h， 生成 Acetic acid (5S,7S,8R,8aS)-5-[3-(2,6-bis-benzyloxy-pyrimidin-4-yl)-2-nitro-propyl]-3-ethoxy-8-methyl-1,5,6,7,8,8a-hexahydro-imidazo[1,5-a]pyridin-7-yl ester
  参考文献：
  名称：

  7-脱氧cylindrospermopsin的推定结构的合成：抑制蛋白质合成不需要C7氧合。

  摘要：

  DOI：

  10.1002/anie.200500520
• 作为产物：
  描述：

  2,4,6-三溴嘧啶 、 苯甲醇 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以80%的产率得到4-溴-2,6-双(苯基甲氧基)嘧啶
  参考文献：
  名称：

  Syntheses of the cylindrospermopsin alkaloids

  摘要：

  An intramolecular 1,3-dipolar cycloaddition has efficiently constructed the A-ring portions of the cylindrospermopsin alkaloids. A nitro-aldol addition of an elaborated nitroalkane to a pyrimidine aldehyde followed by an intramolecular reductive guanidinylation has enabled the syntheses of all three alkaloids in this family in 18-19 steps. We report the first asymmetric synthesis of cylindrospermopsin, unambiguously assigning its absolute configuration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.044

文献信息

• Vinyl and Alkynyl Pyrimidines as Michael Acceptors:  An Approach to a Cylindrospermopsin Substructure
  作者：Jane F. Djung、David J. Hart、Erick R. R. Young

  DOI：10.1021/jo000504f

  日期：2000.9.1

  base-mediated intramolecular conjugate addition reactions in which a carbamate and a urea, respectively, behave as nitrogen nucleophiles. The cyclic carbamate derived from 9 was converted to 11 via a metalation-oxidation reaction in which 2-phenylsulfonyl-3-phenyloxaziridine behaves as a hydroxylation reagent. The cyclic urea derived from 24 was converted to cylindrospermopsin substructure 30 using dimethyldioxirane

  乙烯基嘧啶9和炔基嘧啶24经历碱介导的分子内共轭加成反应，其中氨基甲酸酯和尿素分别充当氮亲核试剂。由9衍生的环状氨基甲酸酯通过金属氧化反应转化为11，其中2-苯基磺酰基-3-苯基恶唑烷充当羟基化试剂。使用二甲基二环氧乙烷引入C（7）羟基，将24衍生的环状脲转化为环精皮子亚结构30。
• Enzyme inhibitors, their synthesis and methods for use
  申请人：el Kouni; Mahmoud H.

  公开号：US05476855A1

  公开（公告）日：1995-12-19

  Novel compounds are provided that are effective to inhibit the activity of DHUDase or UrdPase. Such compounds have the general formula ##STR1## where X is S or Se; Y is I, F, Cl, Br, methoxy, benzyl, selenenylphenyl, or thiophenyl, and R.sub.1 is an acyclo tail having the general formula ##STR2## where R.sub.2 is H, CH.sub.2 OH or CH.sub.2 NH.sub.2 ; R.sub.3 is OH, NH.sub.2, or OCOCH.sub.2 CH.sub.2 CO.sub.2 H; and R.sub.4 is O, S, or CH.sub.2. The compounds can be used in pharmaceutical compositions, along with various chemotherapeutic agents to increase the efficacy of the treatment. These compounds can also be used in methods of treating patients by coadministering or sequentially administering the enzyme inhibiting compounds with a chemotherapeutic agent effective to treat cancers, or viral, fungal, bacterial, or parasitic infections. The compounds have further utility in enhancing imaging. Further, they can be administered alone to prevent and/or treat disorders of pyrimidine catabolism and other physiological disorders.

  提供了一种新型化合物，可有效抑制DHUDase或UrdPase的活性。这些化合物具有一般式 ##STR1## 其中 X 是 S 或 Se；Y 是 I、F、Cl、Br、甲氧基、苄基、硒苯基或噻吩基，R.sub.1 是具有一般式 ##STR2## 的醋酸尾部，其中 R.sub.2 是 H、CH.sub.2 OH 或 CH.sub.2 NH.sub.2 ；R.sub.3 是 OH、NH.sub.2 或 OCOCH.sub.2 CH.sub.2 CO.sub.2 H；R.sub.4 是 O、S 或 CH.sub.2。这些化合物可以与各种化疗药物一起用于制备药物组合物，以增加治疗的功效。这些化合物还可以用于通过联合给药或顺序给药酶抑制化合物和有效治疗癌症、病毒、真菌、细菌或寄生虫感染的化疗药物来治疗患者的方法。这些化合物还可以用于增强成像。此外，它们可以单独用于预防和/或治疗嘧啶分解和其他生理紊乱。
• Phenylselenenyl- and phenylthio-substituted pyrimidines as inhibitors of dihydrouracil dehydrogenase and uridine phosphorylase
  作者：Naganna M. Goudgaon、Fardos N. M. Naguib、Mahmoud H. el Kouni、Raymond F. Schinazi

  DOI：10.1021/jm00078a015

  日期：1993.12

  Lithiation of 5-bromo-2,4-bis (benzyloxy) pyrimidine (3) with n-BuLi at -80 degrees C followed by the addition of diphenyl diselenide or diphenyl disulfide as an electrophile furnished the corresponding 5-(phenylhetera)-2,4-bis(benzyloxy) pyrimidine, which on exposure to trimethylsilyl iodide in CH2-Cl-2 at room temperature yielded the 5-(phenylhetera)uracils in 70-75% yield. Similarly, the 6-(phenylhetera) uracils were prepared from 6-bromo-2,4-bis (benzyloxy) pyrimidine (10). 1-[(2-Hydroxyethoxy)methyl] -5-(phenylselenenyl)uracil (PSAU, 18) and 1-(ethoxymethyl)-5- (phenylselenenyl)uracil (17) were synthesized by the electrophilic addition of benzeneselenenyl chloride to the acyclic uracils under basic conditions. These compounds were evaluated for their ability to inhibit dihydrouracil dehydrogenase (DHUDase, E.C. 1.3.1.2), orotate phosphoribosyltransferase (OPRTase, E.C. 2.4.2.10), uridine phosphorylase (UrdPase, E.C. 2.4.2.3), and thymidine phosphorylase (dThdPase, E.C. 2.4.2.4). 5-(Phenylselenenyl)uracil (PSU, 6) and 5-(phenylthio)uracil (PTU, 7) inhibited DHUDase with apparent K-i values of 4.8 and 5.4 mu M, respectively. The corresponding 6-analogues, compounds 13 and 14, demonstrated inhibitory activity against OPRTase. PTU as well as PSU and its riboside, 2'-deoxyriboside, and acyclonucleosides were inhibitors of UrdPase, with PSAU (18) being the most potent with an apparent K-i value of 3.8 mu M. None of the compounds evaluated had any effect on dThdPase. Interestingly, most of the compounds showed modest selective anti-human-immunodeficiency-virus activity in acutely infected primary human lymphocytes.
• YAMAMOTO, YOSHINORI;SEKO, TOSHIYA;NEMOTO, HISAO, J. ORG. CHEM., 54,(1989) N0, C. 4376-4734
  作者：YAMAMOTO, YOSHINORI、SEKO, TOSHIYA、NEMOTO, HISAO

  DOI：——

  日期：——
• Goudgaon Naganna M., Naguib Fardos N. M., Kouni Mahmoud H. el, Schimazi R+, J. Med. Chem, 36 (1993) N 26, S 4250-4254
  作者：Goudgaon Naganna M., Naguib Fardos N. M., Kouni Mahmoud H. el, Schimazi R+

  DOI：——

  日期：——