11-(n-butoxy)-1-undecyne | 372167-89-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 11-(n-butoxy)-1-undecyne
• 英文别名: 11-n-butyloxy-1-undecyne；11-butyloxy-1-undecyne；11-Butoxyundec-1-yne
• CAS: 372167-89-0
• 化学式: C₁₅H₂₈O
• 分子量: 224.387
• InChiKey: OZHSCURWHLVSQO-UHFFFAOYSA-N

物化性质

• 沸点：
  284.5±13.0 °C(Predicted)
• 密度：
  0.842±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  11-(n-butoxy)-1-undecyne 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 3-(2-deoxy-β-D-ribofuranosyl)-6-(9-(butoxy)nonyl)-2,3-dihydrofuro[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  Novel bicyclic furanopyrimidines with dual anti-VZV and -HCMV activity

  摘要：

  Several novel bicyclic furanopyrimidine deoxy nucleosides have been designed, prepared and evaluated as anti-Varicella Zoster Virus agents. The compounds have long ether side chains. Uniquely amongst compounds of this family to date the present agents show dual anti- (VZV) and human cytomegalovirus (HCMV) activity. The lead compounds inhibit VZV at 10 nM and HCMV at 5 muM. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.028
• 作为产物：
  描述：

  10-十一炔醇 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 37.08h， 生成 11-(n-butoxy)-1-undecyne
  参考文献：
  名称：

  Novel Antiviral Activity of l-Dideoxy Bicyclic Nucleoside Analogues versus Vaccinia and Measles Viruses in Vitro

  摘要：

  Dideoxy bicyclic pyrimidine nucleoside analogues (ddBCNAs) with D-chirality have previously been described by us to inhibit replication of human cytomegalovirus. We herein report for the first time that activity against vaccinia virus (VACV) was achieved using novel L-analogues. A structure-activity relationship was established: Antiviral activity versus VACV was highest with an ether side chain with an optimum of n-C9H18-O-n-C5H11. This gave an IC50 of 190 nM, a 60-fold enhancement over the FDA-approved antiviral cidofovir. Interestingly, L-ddBCNAs also inhibit wild type measles virus syncytia formation with a TCID50 of 7.5 mu M for the lead compound. We propose that L-ddBCNAs represent significant innovative antiviral candidates versus measles and poxviruses, and we suggest a mechanism of action versus one or more cellular targets that are essential for viral replication.

  DOI：

  10.1021/jm301778x

文献信息

• [EN] CONDENSED PYRIMIDINE NUCLEOSIDE ANALOGS AS ANTI -VIRAL AGENTS<br/>[FR] ANALOGUES DE NUCLÉOSIDES DE PYRIMIDINE CONDENSÉS EN TANT QU'AGENTS ANTIVIRAUX
  申请人：UNIV CARDIFF

  公开号：WO2013007992A1

  公开（公告）日：2013-01-17

  3-(2',3'-dideoxy-ribo-β-L-furanosyl)[2,3-d]pyrimidin-2(3H)-one derivatives comprising 6-substitutents on the base moiety are shown to have anti-viral properties, particularly with respect to vaccinia and measles. The compounds have unnatural L ribose stereochemistry.

  已知在嘌呤碱基部分具有6-取代基的3-(2',3'-二去氧-β-L-呋喃核苷基)[2,3-d]嘧啶-2(3H)-酮衍生物具有抗病毒性能，特别是针对天花病毒和麻疹病毒。这些化合物具有非天然的L核糖立体化学结构。
• CHEMICAL COMPOUNDS
  申请人：McGuigan Christopher

  公开号：US20130012468A1

  公开（公告）日：2013-01-10

  3-(2′,3′-dideoxy-ribo-β-L-furanosyl)[2,3-d]pyrimidin-2(3H)-one derivatives comprising 6-substitutents on the base moiety are shown to have anti-viral properties, particularly with respect to vaccinia and measles. The compounds have unnatural L ribose stereochemistry.

  在碱基部分上含有6-取代基的3-(2′,3′-二脱氧-β-L-呋喃核糖基)[2,3-d]嘧啶-2(3H)-酮衍生物显示出抗病毒特性，特别是对天花病毒和麻疹病毒。这些化合物具有非自然的L-核糖立体化学结构。
• Anti-viral pyrimidine nucleoside analogues
  申请人：——

  公开号：US20030176370A1

  公开（公告）日：2003-09-18

  A compound, which can show potent anti-viral activity against, for example, cytomegalo virus, has the formula (I), wherein R is selected from the group comprising, optionally substituted, C 5 to C 20 alkyl and, optionally substituted, C 5 to C 20 cycloalkyl; R′ is selected from the group comprising hydrogen, alkyl, cycloalkyl, halogens, amino, alkylamino, dialkylamino, nitro, cyano, alkyoxy, aryloxy, thiol, alkylthiol, arythiol, alkyl; R″ is selected from the group comprising hydrogen, alkyl, cycloalkyl, halogens, alkyloxy, aryloxy and aryl; Q is selected from the group comprising O, NH, S, N-alkyl and CY 2 , where Y may be the same or different and is selected from H, alkyl and halogens; X is selected from the group comprising O, NH, S, Se, N-alkyl, (CH 2 ) n where n is 1 to 10, and CY 2 where Y may be the same or different and is selected from hydrogen, alkyl and halogens; Z is selected from the group comprising O, S, NH, and N-alkyl; T is selected from the group comprising H, halogens, alkyl (C 1 to C 10 ), O-alkyl (C 1 to C 10 ), N 3 and CN; T′ is selected from the group comprising H, halogens, O-alkyl (C 1 to C 10 ), N 3 and CN; or T and T′ together form a bridge which is selected from the group comprising —O—, —NH— and —(CH 2 ) p — wherein p is an integer from 1 to 6; T″ is selected from the group comprising H, OH, halogens, N 3 and CN; T′″ is selected from the group comprising H, OH, halogens, N 3 and CN; or T″ and T′″ together form a bridge which is selected from the group comprising —O—, —NH— and —(CH 2 ) p — wherein p is an integer from 1 to 6; or T and T′″ together form ═CH 2 ; and W is selected from the group comprising H, a phosphate group a phosphonate group; and a pharmacologically acceptable salt derivative or pro-drug thereof.

  一种可对例如巨细胞病毒表现出强效抗病毒活性的化合物具有式(I)，其中 R 选自由任选取代的 C 5 至 C 20 烷基和任选取代的 C 5 至 C 20 R′选自包括氢、烷基、环烷基、卤素、氨基、烷基氨基、二烷基氨基、硝基、氰基、烷氧基、芳氧基、硫醇、烷硫醇、芳硫醇、烷基在内的组；R″选自包括氢、烷基、环烷基、卤素、烷氧基、芳氧基和芳基在内的组；Q 选自包括 O、NH、S、N-烷基和 CY 2 其中 Y 可以相同或不同，选自 H、烷基和卤素； X 选自包括 O、NH、S、Se、N-烷基、(CH2) 2 ) n 其中 n 为 1 至 10，以及 CY 2 其中 Y 可以相同或不同，选自氢、烷基和卤素；Z 选自 O、S、NH 和 N-烷基；T 选自 H、卤素、烷基（C 1 至 C 10 ）、O-烷基（C 1 至 C 10 ), N 3 和 CN；T′选自包括 H、卤素、O-烷基（C 1 至 C 10 ), N 3 和 CN；或 T 和 T′共同形成一个桥，该桥选自包括 -O-、-NH- 和 -(CH)在内的组。 2 ) p - 其中 p 是 1 到 6 的整数；T″ 选自包括 H、OH、卤素、N 3 和 CN 所组成的组； T′″ 选自包括 H、OH、卤素、N 3 和 CN 所组成的组；或 T″ 和 T′″ 一起形成一个桥，该桥选自由 -O-、-NH- 和 -(CH 2) 组成的组。 2 ) p - 其中 p 是 1 到 6 的整数；或 T 和 T′″一起形成 ═CH 2 和 W 选自包括 H、磷酸基团、膦酸基团和药理学上可接受的盐衍生物或其原药的组。
• ANTI-VIRAL PYRIMIDINE NUCLEOSIDE ANALOGUES
  申请人：University College Cardiff Consultants Limited

  公开号：EP1280813A1

  公开（公告）日：2003-02-05
• CONDENSED PYRIMIDINE NUCLEOSIDE ANALOGS AS ANTI-VIRAL AGENTS
  申请人：University College Cardiff Consultants, Ltd.

  公开号：EP2729153B1

  公开（公告）日：2015-09-16