10-azide-1-decyne | 1443143-97-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 10-azide-1-decyne
• 英文别名: 10-azido-1-decyne；10-Azidodec-1-yne
• CAS: 1443143-97-2
• 化学式: C₁₀H₁₇N₃
• 分子量: 179.265
• InChiKey: KTURKGRXOOFQQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-azide-1-decyne 在 吡啶 、 4-二甲氨基吡啶 、 sodium periodate 、 Zn(OTf)₂ 、 (1S,2R)-(+)-N-methylephedrine 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 67.5h， 生成 (R)-1-((2R,5R)-5-{(R)-10-[5-(dimethylamino)naphthalene-1-sulfonamido]-1-hydroxydec-2-ynyl}tetrahydrofuran-2-yl)-11-(thiophene-3-carboxamido)undec-2-ynyl acetate
  参考文献：
  名称：

  Synthesis of dansyl-labeled probe of thiophene analogue of annonaceous acetogenins for visualization of cell distribution and growth inhibitory activity toward human cancer cell lines

  摘要：

  The convergent synthesis of the dansyl-labeled probe of the thiophene-3-carboxamide analogue of annonaceous acetogenins, which shows potent antitumor activity, was accomplished by two asymmetric alkynylations of the 2,5-diformyl THF equivalent with an alkyne having a thiophene moiety and another alkyne tagged with a dansyl group. The growth inhibitory profiles toward 39 human cancer cell lines revealed that the probe retained the biological function of its mother compound, and would be useful for studying cellular activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.037
• 作为产物：
  描述：

  2-癸炔-1-醇 在 咪唑 、 sodium azide 、 碘 、 sodium hydride 、 1,3-丙二胺 、 三苯基膦 作用下， 以 二氯甲烷 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 2.67h， 生成 10-azide-1-decyne
  参考文献：
  名称：

  Synthesis of dansyl-labeled probe of thiophene analogue of annonaceous acetogenins for visualization of cell distribution and growth inhibitory activity toward human cancer cell lines

  摘要：

  The convergent synthesis of the dansyl-labeled probe of the thiophene-3-carboxamide analogue of annonaceous acetogenins, which shows potent antitumor activity, was accomplished by two asymmetric alkynylations of the 2,5-diformyl THF equivalent with an alkyne having a thiophene moiety and another alkyne tagged with a dansyl group. The growth inhibitory profiles toward 39 human cancer cell lines revealed that the probe retained the biological function of its mother compound, and would be useful for studying cellular activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.037

文献信息

• Structure–activity relationships of hybrid annonaceous acetogenins: Powerful growth inhibitory effects of their connecting groups between heterocycle and hydrophobic carbon chain bearing THF ring on human cancer cell lines
  作者：Naoto Kojima、Tetsuya Fushimi、Takahiro Tatsukawa、Takehiko Yoshimitsu、Tetsuaki Tanaka、Takao Yamori、Shingo Dan、Hiroki Iwasaki、Masayuki Yamashita

  DOI：10.1016/j.ejmech.2013.03.009

  日期：2013.5

  Five novel hybrid molecules of annonaceous acetogenins and insecticides targeting mitochondrial complex I were synthesized and their growth inhibitory activities against 39 human cancer cell lines were investigated. It was revealed that the connecting group between the N-methylpyrazole part and the hydrophobic alkyl chain bearing the THF ring influenced their biological activities significantly. Amide-connected

  合成了针对线粒体复合体I的五种新的杂种产乙酸原和杀虫剂杂合分子，并研究了它们对39种人类癌细胞系的生长抑制活性。揭示了N-甲基吡唑部分和带有THF环的疏水烷基链之间的连接基团显着影响了它们的生物学活性。尤其是，与酰胺连接的类似物2对某些癌细胞系表现出选择性且非常有效的活性（<10 nM）。
• Structure–antitumor activity relationship of hybrid acetogenins focusing on connecting groups between heterocycles and the linker moiety
  作者：Kaito Ohta、Tetsuya Fushimi、Mutsumi Okamura、Akinobu Akatsuka、Shingo Dan、Hiroki Iwasaki、Masayuki Yamashita、Naoto Kojima

  DOI：10.1039/d2ra02399g

  日期：——

  The in vivo active 1-methylpyrazole-5-sulfonamide analog of acetogenins was obtained by the structure–antitumor activity relationship, focusing on the connecting groups between the heterocycle and the linker.

  通过结构-抗肿瘤活性关系，重点关注杂环和连接剂之间的连接基团，得到了1-甲基吡唑-5-磺酰胺类乙酰甘氨酸的体内活性类似物。