亚砜化合物的生物活性研究和不对称合成进展

doi:10.6023/cjoc202103046

摘要/Abstract

亚砜类化合物在有机合成和药物化学中有着广泛的应用, 手性亚砜作为助剂、配体、催化剂和合成子的用途已得到充分证明, 亚砜类化合物的亚磺酰基团也可作为药效团、羰基生物等排体或药物分子修饰基团应用于药物设计和药物开发之中. 综述了具有生物活性的亚砜类化合物的结构骨架以及相应的作用机制, 并总结了近十年来通过构建硫立体中心制备手性亚砜类化合物的新方法和新进展, 具体到廉价金属铁络合物、多金属氧酸盐、有机小分子、生物酶和电化学催化的硫醚不对称氧化反应, 以及基于次磺酸阴离子中间体的手性亚砜合成策略和最近涌现的新策略, 其中也包括作者最近在手性亚砜合成领域取得一些研究成果.

关键词: 亚砜生物活性分子, 亚砜药物, 不对称合成, 硫醚氧化反应, 次磺酸阴离子, 多金属氧酸盐

Sulfoxide compounds bearing unique sulfinyl group have attracted extensive attentions due to their important application in asymmetric organic synthesis and medicinal chemistry. The utility of chiral sulfoxides as versatile auxiliaries, ligands, and catalysts and synthons has been well demonstrated. Furthermore, the sulfinyl moiety can act as a pharmaceutical core, a bioisosteric replacement of the carbonyl moiety or a modifier in drug design and drug development. In this review, their biological activities with esomeprazole, ajoene, sulforaphane, sulforaphene, cenicriviroc, arbidol sulfoxide, armodafinil and so on are exemplified. And their mechanisms of action are illustrated briefly. Since the sulfur chirality is different from carbon stereogenic center, much effort has been devoted to the preparation of chiral sulfoxides. Herein the advances in asymmetric synthesis of sulfoxide during the past decade are presented. The direct asymmetric oxidation of prochiral sulfides with cheap iron-complex catalyst, polyoxometalates, organocatalyst, biocatalyst and electrocatalyst is discussed. Moreover, the complementary strategy based on sulfenate anions and miscellaneous strategies emerged recently are described. Additionally, our recent research works in the construction of chiral sulfoxide are also mentioned.

Key words: bioactive sulfoxide, sulfoxide drug, asymmetric synthesis, sulfoxidation, sulfenate anion, polyoxometalates

引用此文

朱海梦, 王超, 宗利利. 亚砜化合物的生物活性研究和不对称合成进展[J]. 有机化学, 2021, 41(9): 3431-3447.

Haimeng Zhu, Chao Wang, Lili Zong. Progress on Biological Activity Study and Enantioselective Synthesis of Sulfoxides[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3431-3447.

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图/表 27

图1. 亚砜类化合物的结构和应用

Figure 1. Structure and application of sulfoxides

图2. 亚砜类质子泵抑制剂的结构式

Figure 2. Structures of sulfoxides-type proton pump inhibitors

图式1. 埃索美拉唑对H+K+-ATPase质子泵的抑制机制

Scheme 1. Esomeprazole for H+K+-ATPase inhibition

图式2. 阿焦烯的生物合成路线

Scheme 2. Biosynthetic route to ajoene

图式3. 阿焦烯以及其衍生物的化学合成路线

Scheme 3. Synthetic route to ajoene and its analogues

图式4. 萝卜硫素和莱菔素的生物合成路线

Scheme 4. Biosynthesis of Sulforaphane and Sulforaphene

图式5. 莱菔素衍生物

Scheme 5. Sulforaphene derivative

图式6. 乙烯基亚砜类化合物

Scheme 6. Vinyl sulfoxide compounds

图3. Cenicriviroc及其衍生物

Figure 3. Cenicriviroc and its derivatives

图4. 阿比多尔及其亚砜衍生物

Figure 4. Arbidol and its sulfoxide analogues

图5. 阿莫达菲尼及其衍生物

Figure 5. Armodafinil and its derivatives

图6. 舒林酸和其他具有生物活性的亚砜

Figure 6. Sulindac and other bioactive sulfoxides

图7. 具有生物活性的杂芳基亚砜和环亚砜

Figure 7. Bioactive heteroaromatic and cyclic sulfoxides

图式7. Anderson法和Kagan-Modern法制备手性亚砜

Scheme 7. Anderson method and Kagan-Moderna method

图8. 手性亚砜的合成路径

Figure 8. Synthetic approaches to chiral sulfoxides

图式8. 铁络合物催化的硫醚不对称氧化反应

Scheme 8. Iron-catalyzed asymmetric sulfoxidation

图式9. 多金属氧酸盐催化的硫醚不对称氧化反应

Scheme 9. Asymmetric sulfoxidation catalyzed by polyoxometalates

图式10. 有机小分子催化的硫醚不对称氧化反应

Scheme 10. Organocatalyst for asymmetric sulfoxidation

图式11. 生物催化氧化法应用于中试生产(S)-奥美拉唑

Scheme 11. Pilot-scale biocatalytic sulfoxidation for (S)-omerprazole

图式12. 电化学法硫醚不对称氧化反应

Scheme 12. Electrochemical asymmetric sulfoxidation

图式13. 经由次磺酸阴离子合成手性亚砜

Scheme 13. Approaches to sulfenate anion towards sulfoxide synthesis

图式14. Pd催化的不对称芳基化和烯基化反应

Scheme 14. Arylation/alkenylation of sulfenate anion catalyzed by Pd complex catalysts

图式15. 相转移催化的不对称烷基化反应

Scheme 15. Alkylation of sulfenate anion catalyzed by phase-transfer catalysis

图式16. 其他策略

Scheme 16. Miscellaneous strategies

图式17. 动力学拆分策略

Scheme 17. Kinetic resolution of racemic sulfoxide

图式18. 去对称化和平行动力学拆分

Scheme 18. Desymmetrization and parallel kinetic resolution

图式19. 光致去外消旋化策略

Scheme 19. Photochemical deracemization

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