5-(5-bromothien-2-yl)-1-(β-D-2-deoxyribofuranos-1-yl)uracil | 134333-70-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-(5-bromothien-2-yl)-1-(β-D-2-deoxyribofuranos-1-yl)uracil
• 英文别名: 5-(5-bromo-2-thienyl)-2'-deoxyuridine；5-(5-bromothien-2-yl)-2'-deoxyuridine；5-bromothienyldeoxyuridine；5-(5-bromothiophen-2-yl)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 134333-70-3
• 化学式: C₁₃H₁₃BrN₂O₅S
• 分子量: 389.227
• InChiKey: IGUZFFOBAZCVRK-VAOFZXAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  127
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(5-bromothien-2-yl)-1-(β-D-2-deoxyribofuranos-1-yl)uracil 在 溴 作用下， 生成 5-(3,5-Dibromo-thiophen-2-yl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Antiviral Activities of Some New 5-Heteroaromatic Substituted Derivatives of 2'-Deoxyuridine

  摘要：

  Eight new 5-heteroaromatic substituted analogues of 2'-deoxyuridine have been synthesized and evaluated for their inhibitory properties against a panel of different viruses. Several analogues containing a substituted thiophene moiety proved to be highly selective against herpes simplex virus type 1 (HSV-1).

  DOI：

  10.1080/15257779508012418
• 作为产物：
  描述：

  碘苷 在 吡啶 、 palladium diacetate 、 氨 、 溴 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 四氯化碳 、 氯仿 为溶剂， 反应 20.0h， 生成 5-(5-bromothien-2-yl)-1-(β-D-2-deoxyribofuranos-1-yl)uracil
  参考文献：
  名称：

  5-(5-Bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothien-2-yl)-2'-deoxyuridine are equipotent to (E)-5-(2-bromovinyl)-2'-deoxyuridine in the inhibition of herpes simplex virus type I replication

  摘要：

  2'-Deoxyuridines with a five-membered heterocyclic substituent in the 5-position were synthesized by palladium-catalyzed coupling reactions of 5-iodo-2'-deoxyuridine with the activated heteroaromatics. Further modification of the compound with the 5-thien-2-yl substituent gave 5-(5-bromothien-2-yl)-2'-deoxyuridine and 5-(5-chlorothienyl-2-yl)-2'-deoxyuridine. Both compounds show potent and selective activity against herpes simplex virus type 1 and varicella-zoster virus.

  DOI：

  10.1021/jm00112a011

文献信息

• Synthesis and in vitro antileishmanial activity of 5-substituted-2′-deoxyuridine derivatives
  作者：Corinne Peyron、Rachid Benhida、Christian Bories、Philippe M. Loiseau

  DOI：10.1016/j.bioorg.2005.07.001

  日期：2005.12

  We report herein the synthesis and the in vitro antileishmanial evaluation of 5-substituted-2'-deoxyuridine nucleosides. The most active compound against Leishmania donovani promastigotes was Thia-dU (3a) with an IC50 = 3 mu M. This compound exhibited the same activity as zidovudine (3'-azido-2'-deoxythymidine) used as nucleoside reference compound. Considering the cytotoxicity of synthetic compounds on peritoneal murine macrophages., the most toxic compound was MeThio-dU (3d) with a MTC at 10 mu M. Only Methia-dU (3b) was active against intramacrophagic amastigotes with an IC50 = 6.5 mu M. This latter can now be evaluated in vivo, for further investigations through structure-based drug design. (c) 2005 Elsevier Inc. All rights reserved.
• EP0804547A4
  申请人：——

  公开号：EP0804547A4

  公开（公告）日：1999-11-03
• UNIQUE ASSOCIATED KAPOSI'S SARCOMA VIRUS SEQUENCES AND USES THEREOF
  申请人：The Trustees of Columbia University in the City of New York

  公开号：EP0804547A1

  公开（公告）日：1997-11-05
• EP0934333A4
  申请人：——

  公开号：EP0934333A4

  公开（公告）日：1999-11-03
• Unique associated Kaposi's sarcoma virus sequences and uses thereof
  申请人：Chang Yuan

  公开号：US20090022748A1

  公开（公告）日：2009-01-22

  This invention provides an isolated peptide encoded by a nucleic acid which is at least 30 nucleotides in length and has a sequence which uniquely defines a herpesvirus associated with Kaposis' sarcoma, which herpesvirus is present in and recoverable from the HBL-6 cell line (ATCC Accession No. CRL 11762).