(S)-naproxen propionate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-naproxen propionate
• 英文别名: (S)-(2-propinyl)-2-(6-methoxy-2-naphthyl)propionate；(S)-Naproxen-propargylester；prop-2-ynyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: RPLLXWJHCSDOLS-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dicobalt octacarbonyl 、 (S)-naproxen propionate 以 四氢呋喃 为溶剂， 以56%的产率得到hexacarbonyl[(S)-(2-propinyl)-2-(6-methoxy-2-naphthyl)propionate]dicobalt
  参考文献：
  名称：

  Acetylenehexacarbonyldicobalt complexes, a novel class of antitumor drugs

  摘要：

  Acetylenehexacarbonyldicobalt bait complexes were synthesized and tested for antitumor activity. The MCF-7 and MDA-MB-231 mammary tumor cell lines and the LNCaP/FGC prostate carcinoma cell line were used as in vitro models. The structural evaluation was performed by IR and NMR spectroscopy and revealed a change of the linear acetylene core to a structure comparable to Z-olefins after coordination to the cobalt centers. In cell culture experiments the strongest effects were found for hexacarbonyl[2-propinylacetylsalicylate] (10), which was more active than cisplatin on the human mammary tumor cell lines MCF-7 and MDA-MB-231 in each concentration tested (a 5 mu M concentration of this compound even caused cytocidal effects). In contrast to this, 10 influenced the growth of the LNCaP/FGC cells only marginally, even in the highest concentration. The mode of action of the complexes tested is unknown. As the cobalt complexes show strong antiproliferative effects and their ligands do not it could be unambiguously demonstrated that complex formation is essential to achieve cytotoxic effects. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0020-1693(00)00139-0

文献信息

• 10.1038/s41557-024-01535-8
  作者：Li, Xiangdong、Wodrich, Matthew D.、Waser, Jérôme

  DOI：10.1038/s41557-024-01535-8

  日期：——

  cyclopropenyl-gold(III) species as equivalents of σ-type CPCs, which can then react with terminal alkynes and vinylboronic acids. With catalyst loadings as low as 2 mol%, the synthesis of highly functionalized alkynyl- or alkenyl-cyclopropenes proceeded under mild conditions. A class of hypervalent iodine reagents—the cyclopropenyl benziodoxoles (CpBXs)—enabled the direct oxidation of gold(I) to gold(III) with concomitant

  环丙烯是最小的不饱和碳环。从环丙烯中去除一个取代基可得到环丙烯阳离子（C3+ 系统，CPC）。1957 年，Breslow 通过去除脂肪族位点上的取代基发现了稳定的芳香族 π 型 CPC。相比之下，σ型 CPC（通过去除烯烃上的一个取代基正式获得）不稳定且相对未被探索。在这里，我们介绍了亲电环丙烯基金 （III） 物质作为 σ 型 CPC 的等价物，然后可以与末端炔烃和乙烯基硼酸反应。在催化剂负载量低至 2 mol% 的情况下，在温和条件下进行高度官能化的炔基或烯基环丙烯的合成。一类高价碘试剂——环丙烯基苯并氧唑 （CpBX）——能够直接将金 （I） 氧化成金 （III），同时发生环丙烯基团的转移。该方案是通用的，对许多官能团具有耐受性，可用于复杂天然产物、生物活性分子和药物的后期修饰。
• Synthesis of Optically Active Tetrahedral Clusters through Ester Exchange Catalyzed by Lipase
  作者：Quan-Yi Zhao、Wei-Qiang Zhang、Yu-Hua Zhang、Bin Hu、Yuan-Qi Yin、Chun-Gu Xia

  DOI：10.1021/om034204a

  日期：2004.2.1

  Reactions of the monoanions [(eta(5) -C5H4R)M-2(CO)(3)](-) with ArCH(Me)COOCH2C2H(mu(3)-C)Co-2(CO)(6) (4) in THF at 60 degreesC gave the functional cluster derivatives ArCH(Me)COOCH2C2H(mu3-C)CoM2(CO)(5)(eta(5)-C5H4R) (1a-d: M-2 = Mo, W; R = CO2Me, C(O)Me). Similarly, reactions of [(eta(5)-C5H4)C(O)OCH2(OH)CH3]M-2(CO)(3)}(-) (M-2 = Mo, W) with (mu(3)-S)M1Co2(CO)(9) (M-1 = Fe, Ru) gave the tetrahedral metal clusters (mu(3)-S)CoM2M1(CO)(8)[(eta(5)-C5H4)C(O)OCH2(OH)CH3] (8a-d: M-1 = Fe, Ru; M-2 = Mo, W). Treatment of the two metal clusters 1a-d and three metal clusters 8a-d with methanol respectively in the presence of lipase at 50 degreesC for 1 h afforded the optically active cluster derivatives HOCH2C2H(mu(3)-C)CoM2(CO)(5)(eta(5)-C5H4R) (6a-d: M-2 = Mo, W; R = CO2Me, C(O)Me) and (mu(3)-S)CoM2M1(CO)(8)[eta(5)-C5H4)C(O)OCH3] (9a-d: M, = Fe, Ru; M-2 = Mo, W)- The products were separated by silica gel chromatography. The conditions of the lipase reactions were discussed. All the compounds in the global process were characterized by element analysis, and IR and H-1 NMR spectroscopy. The structures of clusters 8c and 9c have been determined by single-crystal X-ray diffraction.
• Acetylenehexacarbonyldicobalt complexes, a novel class of antitumor drugs
  作者：Kathrin Schmidt、Manfred Jung、Roland Keilitz、Beate Schnurr、Ronald Gust

  DOI：10.1016/s0020-1693(00)00139-0

  日期：2000.8

  Acetylenehexacarbonyldicobalt bait complexes were synthesized and tested for antitumor activity. The MCF-7 and MDA-MB-231 mammary tumor cell lines and the LNCaP/FGC prostate carcinoma cell line were used as in vitro models. The structural evaluation was performed by IR and NMR spectroscopy and revealed a change of the linear acetylene core to a structure comparable to Z-olefins after coordination to the cobalt centers. In cell culture experiments the strongest effects were found for hexacarbonyl[2-propinylacetylsalicylate] (10), which was more active than cisplatin on the human mammary tumor cell lines MCF-7 and MDA-MB-231 in each concentration tested (a 5 mu M concentration of this compound even caused cytocidal effects). In contrast to this, 10 influenced the growth of the LNCaP/FGC cells only marginally, even in the highest concentration. The mode of action of the complexes tested is unknown. As the cobalt complexes show strong antiproliferative effects and their ligands do not it could be unambiguously demonstrated that complex formation is essential to achieve cytotoxic effects. (C) 2000 Elsevier Science S.A. All rights reserved.