2-(3-{2-[3-(Naphthalen-2-ylsulfanyl)-prop-1-ynyl]-phenyl}-prop-2-ynyloxy)-tetrahydro-pyran | 176384-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(3-{2-[3-(Naphthalen-2-ylsulfanyl)-prop-1-ynyl]-phenyl}-prop-2-ynyloxy)-tetrahydro-pyran
• CAS: 176384-87-5
• 化学式: C₂₇H₂₄O₂S
• 分子量: 412.552
• InChiKey: JHWPSGGDVINBHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(3-{2-[3-(Naphthalen-2-ylsulfanyl)-prop-1-ynyl]-phenyl}-prop-2-ynyloxy)-tetrahydro-pyran 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-[2-(3-Naphthalen-2-ylsulfonylprop-1-ynyl)phenyl]prop-2-yn-1-ol
  参考文献：
  名称：

  Allene-Eneyne Related Cycloaromatization: Design and Synthesis of New DNA-Cleaving Compounds

  摘要：

  Abstract(Z)‐7‐Sulfonyl‐3‐hexen‐1,5‐diyne containing molecules are stable at room temperature and isomerized to eneyne‐allene‐sulfones under alkaline conditions. These eneyne‐allene‐sulfones were not isolable, spontaneously cyclized to form biradical intermediates under mild conditions, and exhibited good DNA‐cleaving and human tumor cell line growth inhibition properties. Further studies indicated that compounds bearing on aromatic ring at C(3) and C(4), such as 25, proved to be more active against those tumor cell lines. Removal of acetylene unit at C(1) and C(2), made the resulting compound less active. A related compound, (Z,Z)‐12‐(2‐tetrahydropyranyl)oxy‐1‐phenylsulfonyldodeca‐4,8‐diene‐2,6,10‐triyne (37), was synthesized. Upon treatment of triethylamine at refluxing benzene, this compound undergoes double cycloaromatization to form a naphalene adduct, which possesses excellent DNA‐cleaving activity.

  DOI：

  10.1002/jccs.199800072
• 作为产物：
  描述：

  3-{2-[3-(tetrahydropyran-2-yloxy)-prop-1-ynyl]phenyl}prop-2-yn-1-ol 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-(3-{2-[3-(Naphthalen-2-ylsulfanyl)-prop-1-ynyl]-phenyl}-prop-2-ynyloxy)-tetrahydro-pyran
  参考文献：
  名称：

  Allene-Eneyne Related Cycloaromatization: Design and Synthesis of New DNA-Cleaving Compounds

  摘要：

  Abstract(Z)‐7‐Sulfonyl‐3‐hexen‐1,5‐diyne containing molecules are stable at room temperature and isomerized to eneyne‐allene‐sulfones under alkaline conditions. These eneyne‐allene‐sulfones were not isolable, spontaneously cyclized to form biradical intermediates under mild conditions, and exhibited good DNA‐cleaving and human tumor cell line growth inhibition properties. Further studies indicated that compounds bearing on aromatic ring at C(3) and C(4), such as 25, proved to be more active against those tumor cell lines. Removal of acetylene unit at C(1) and C(2), made the resulting compound less active. A related compound, (Z,Z)‐12‐(2‐tetrahydropyranyl)oxy‐1‐phenylsulfonyldodeca‐4,8‐diene‐2,6,10‐triyne (37), was synthesized. Upon treatment of triethylamine at refluxing benzene, this compound undergoes double cycloaromatization to form a naphalene adduct, which possesses excellent DNA‐cleaving activity.

  DOI：

  10.1002/jccs.199800072

文献信息

• Chemical synthesis, DNA cleavage and antitumor activity of molecules with (Z)-7-sulfonyl-3-hexene-1,5-diyne functionalities
  作者：Ming-Jung Wu、Chi-Fong Lin、Chi-Wi Ong

  DOI：10.1016/0960-894x(96)00090-x

  日期：1996.3

  Compounds 20a-d, 21a, 21d and 22 were synthesized from the corresponding (Z)-1,2-dichloroethylene, 1,2-diiodobenzene and 2,3-naphthylene bistriflate respectively and exhibited DNA cleaving properties at 37 degrees C in pH 8.0 as well as potent cytotoxicity against human carcinoma cells with no additive.