(S)-6-(naphthalen-1-yl)-5,6-dihydropyran-2-one | 919296-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-6-(naphthalen-1-yl)-5,6-dihydropyran-2-one
• 英文别名: (S)-6-(naphthalen-1-yl)-5,6-dihydro-2H-pyran-2-one；(6S)-6-(Naphthalen-1-yl)-5,6-dihydro-2H-pyran-2-one；(2S)-2-naphthalen-1-yl-2,3-dihydropyran-6-one
• CAS: 919296-41-6
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: GCNWYKGSIZBJOY-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(naphthalen-1-yl)-but-3-enyl acrylate 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 (S)-6-(naphthalen-1-yl)-5,6-dihydropyran-2-one 、 (R)-6-(naphthalen-1-yl)-5,6-dihydropyran-2-one
  参考文献：
  名称：

  6-Bicycloaryl substituted (S)- and (R)-5,6-dihydro-2H-pyran-2-ones: Asymmetric synthesis, and anti-proliferative properties

  摘要：

  (R)-Goniothalamin, is a member of styryl lactones, possesses selective cytotoxicity against cancer cell lines. In this work, replacement of styryl substituent with 2-naphthyl and 3-quinoyl gave new analogues which may have less conformational changes compared to the lead compound. Anti-proliferative tests indicated that 2-naphthyl substituted (R)-5,6-dihydro-2H-pyran-2-one has slightly better cytotoxicity than (R)-goniothalamin. To clarify the effect of 2-naphthyl substituent additional aryl substituted (R)-5,6-dihydro-2H-pyran-2-ones have been synthesized enantioselectively and tested against PC-3 and MCF-7 cell lines. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.10.069

文献信息

• [EN] A NEW CLASS OF HIGHLY APOPTOTIC ANTI-CANCER AGENTS<br/>[FR] NOUVELLE CLASSE D'AGENTS ANTICANCÉREUX HAUTEMENT APOPTOTIQUES
  申请人：CAGIR ALI

  公开号：WO2011099947A1

  公开（公告）日：2011-08-18

  This invention relates to a list of apoptosis-inducers consisting of 6-bicycloaryl substituted 5,6-dihydro-2H-pyran-2-one derivatives. According to the present invention, the apoptosis-inducers trigger cell death by expression of a list of apoptotic genes, so they can be useful for the treatment of cancers, or other autoimmune diseases suffering from the lack of apoptosis such as viral infections, diabetes type I, or encephalomyelitis.

  这项发明涉及一种由6-双环芳基取代的5,6-二氢-2H-吡喁-2-酮衍生物组成的凋亡诱导剂列表。根据本发明，这些凋亡诱导剂通过表达一系列凋亡基因来触发细胞死亡，因此它们可以用于治疗癌症或其他由于凋亡缺乏而受影响的自身免疫疾病，如病毒感染、1型糖尿病或脑脊髓炎。
• α,β-Unsaturated δ-Lactones from Copper-Catalyzed Asymmetric Vinylogous Mukaiyama Reactions of Aldehydes: Scope and Mechanistic Insights
  作者：Belén Bazán-Tejeda、Guillaume Bluet、Garance Broustal、Jean-Marc Campagne

  DOI：10.1002/chem.200600335

  日期：2006.11.6

  regio-, diastereo-, and enantiocontrolled access to alpha,beta-unsaturated delta-lactones is described, based on the reaction of a silyl dienolate and an aldehyde in the presence of 10 % of Carreira's catalyst. The scope and limitations of this reaction, as well as mechanistic insights concerning the reactivity of an allyl copper species, are discussed.

  基于甲硅烷基二烯酸酯和醛在10％Carreira催化剂存在下的反应，描述了直接的区域，非对映和对映体控制的α，β-不饱和δ-内酯。讨论了该反应的范围和局限性，以及有关烯丙基铜物种反应性的机理见解。
• 6-Bicycloaryl substituted (S)- and (R)-5,6-dihydro-2H-pyran-2-ones: Asymmetric synthesis, and anti-proliferative properties
  作者：Pınar Kasaplar、Özgür Yılmazer、Ali Çağır

  DOI：10.1016/j.bmc.2008.10.069

  日期：2009.1

  (R)-Goniothalamin, is a member of styryl lactones, possesses selective cytotoxicity against cancer cell lines. In this work, replacement of styryl substituent with 2-naphthyl and 3-quinoyl gave new analogues which may have less conformational changes compared to the lead compound. Anti-proliferative tests indicated that 2-naphthyl substituted (R)-5,6-dihydro-2H-pyran-2-one has slightly better cytotoxicity than (R)-goniothalamin. To clarify the effect of 2-naphthyl substituent additional aryl substituted (R)-5,6-dihydro-2H-pyran-2-ones have been synthesized enantioselectively and tested against PC-3 and MCF-7 cell lines. (C) 2008 Elsevier Ltd. All rights reserved.