10-Benzenesulfonyl-deca-2,8-diyn-1-ol | 170877-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 10-Benzenesulfonyl-deca-2,8-diyn-1-ol
• 英文别名: 10-(Benzenesulfonyl)deca-2,8-diyn-1-ol
• CAS: 170877-06-2
• 化学式: C₁₆H₁₈O₃S
• 分子量: 290.383
• InChiKey: PVGHRVIZDYZAQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,8-萘二甲酸酐 、 10-Benzenesulfonyl-deca-2,8-diyn-1-ol 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到Naphthalene-1,8-dicarboxylic acid mono-(10-benzenesulfonyl-deca-2,8-diynyl) ester
  参考文献：
  名称：

  Remarkable tethering effect on DNA cleavage of propargylic sulfone conjugates with intercalating moieties

  摘要：

  A number of novel propargylic sulfone conjugates 3 and 4 with intercalating moieties were synthesized and evaluated for DNA cleavage activity through nucleic base alkylation. A remarkable enhancement in DNA cleaving potency was observed with those conjugates 3 possessing a suitable spacer, a right attachment point at the aromatic ring, and a good intercalator.

  DOI：

  10.1016/s0960-894x(97)10203-7
• 作为产物：
  描述：

  2-(10-Benzenesulfonyl-deca-2,8-diynyloxy)-tetrahydro-pyran 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以85%的产率得到10-Benzenesulfonyl-deca-2,8-diyn-1-ol
  参考文献：
  名称：

  Synthesis, reaction, and cytotoxicity of novel propargylic sulfones

  摘要：

  Propargylic sulfones 1 and 2 have been synthesized for their potent interactions with DNA. The crown ether conjugate 8 was also prepared from 1 under carefully established reaction conditions. The synthesized propargylic sulfones 2, 5, and 8 exhibited high reactivity toward sulfur-, nitrogen-, and oxygen-containing nucleophiles. Compound 1 showed an IC50 of 5.3x10(-6) M against KB/P cancer cells comparable with that of the clinically used agent 5-FU.

  DOI：

  10.1016/0040-4039(95)01169-i

文献信息

• Remarkable tethering effect on DNA cleavage of propargylic sulfone conjugates with intercalating moieties
  作者：Wei-Min Dai、Quan Li、Kin Chiu Fong、Chun Wo Chow、Ling Zhou、Wataru Hamaguchi、Sei-ichi Nishimoto

  DOI：10.1016/s0960-894x(97)10203-7

  日期：1998.1

  A number of novel propargylic sulfone conjugates 3 and 4 with intercalating moieties were synthesized and evaluated for DNA cleavage activity through nucleic base alkylation. A remarkable enhancement in DNA cleaving potency was observed with those conjugates 3 possessing a suitable spacer, a right attachment point at the aromatic ring, and a good intercalator.
• Synthesis, reaction, and cytotoxicity of novel propargylic sulfones
  作者：Wei-Min Dai、Kin Chiu Fong

  DOI：10.1016/0040-4039(95)01169-i

  日期：1995.7

  Propargylic sulfones 1 and 2 have been synthesized for their potent interactions with DNA. The crown ether conjugate 8 was also prepared from 1 under carefully established reaction conditions. The synthesized propargylic sulfones 2, 5, and 8 exhibited high reactivity toward sulfur-, nitrogen-, and oxygen-containing nucleophiles. Compound 1 showed an IC50 of 5.3x10(-6) M against KB/P cancer cells comparable with that of the clinically used agent 5-FU.