稠杂环化合物的合成及其抗肿瘤活性研究进展

doi:10.6023/cjoc202211046

摘要/Abstract

稠杂环化合物具有独特的物理化学性质, 在天然产物全合成、超导材料、储能材料、高分子材料以及有机染料等领域具有广泛应用, 而过渡金属催化是构建碳-碳键及碳-杂键的重要手段之一, 近年来过渡金属催化不饱和烃的反应迅猛发展, 具有合成步骤简单、原子经济性强、原料成本低等特点, 引起了化学家的广泛关注和浓厚研究兴趣. 在此, 总结归纳了近五年涉及过渡金属催化不饱和烃合成苯并呋喃、吲哚、喹啉等稠杂环化合物的反应及其机制，并介绍了稠杂环化合物在抗肿瘤方面的应用.

关键词: 不饱和烃, 过渡金属催化, 稠杂环化合物, 抗肿瘤活性

The unique physicochemical properties invest fused heterocyclic compounds with wide applications in the synthesis of natural products, drugs, superconducting materials, energy storage materials, polymer materials, organic dyes, etc. In recent years, the rapid development of transition metal-catalyzed reactions of unsaturated hydrocarbons has developed rapidly. Owing to the advantages of high step- and atom-economy, easy availability of raw starting materials, and efficient construction of carbon-carbon bonds or/and carbon-hetero bonds, it is a vital way to synthesize fused heterocyclic compounds. Herein, the recent progress on the reaction development of transition metal-catalyzed cyclizations involving unsaturated hydrocarbons for the synthesis of fused heterocyclic compounds including benzofurans, indoles, quinolines in the last five years has been summarized, as well as their applications in the field of medicinal chemistry with antitumor activities.

Key words: unsaturated hydrocarbons, transition metal-catalysis, fused heterocyclic compounds, antitumor activity

引用此文

段康慧, 唐俊龙, 伍婉卿. 稠杂环化合物的合成及其抗肿瘤活性研究进展[J]. 有机化学, 2023, 43(3): 826-854.

Kanghui Duan, Junlong Tang, Wanqing Wu. Recent Advances in the Synthesis of Fused Heterocyclic Compounds and Their Antitumor Activities[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 826-854.

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图/表 76

图1. 2020年销售额前200的含稠杂环结构的药物

Figure 1. Top 200 drugs with fused heterocyclic structure by sales in 2020

图2. 具有生物活性的苯并呋喃类化合物

Figure 2. Benzofurans with biological activity

图式1. 银催化1,6-烯炔与亚磺酸钠环化反应

Scheme 1. Silver-catalyzed cyclization of 1,6-enyne with sodium sulfonate

图式2. 钯催化的串联环化反应

Scheme 2. Palladium-catalyzed tandem cyclization reactions

图式3. 钯催化芳基碘化物与炔烃的环化反应

Scheme 3. Palladium-catalyzed cyclization of aryl iodides and alkynes

图式4. 镍催化合成3-烯基苯并呋喃衍生物

Scheme 4. Nickel-catalyzed synthesis of 3-enylbenzofuran derivatives

图式5. 镍催化未活化烯烃1,2-碳胺化反应

Scheme 5. Nickel-catalyzed 1,2-carboamination of unactivated olefins

图式6. 镍催化烯基醚与环状乙烯基碳酸酯的不对称Heck环化反应

Scheme 6. Nickel-catalyzed asymmetric Heck cyclization of alkenyl ethers with cyclic vinyl ethylene carbonates

图式7. 钯催化烯基醚与炔基肟醚的串联环化反应

Scheme 7. Palladium-catalyzed cascade cyclization of alkenyl ethers with alkynyl oxime ethers

图式8. 铱催化合成多官能团呋喃

Scheme 8. Iridium-catalyzed synthesis of polyfunctional furans

图式9. 具有生物活性的吲哚类化合物

Scheme 9. Indole compounds with biological activity

图式10. 钯催化氮芳基丙烯酰胺不对称Heck环化反应

Scheme 10. Palladium-catalyzed asymmetric Heck cyclization of N-aryl acrylamides

图式11. 钯催化烯烃分子内氧化氨基芳基化反应

Scheme 11. Palladium-catalyzed intramolecular oxidative aminoarylation of olefins

图式12. 银催化偶氮酰亚胺的不对称[3+3]环化反应

Scheme 12. Silver-catalyzed asymmetric [3+3] cyclization of azoimides

图式13. 铜/N,O-配体和BF3?Et2O催化的迈克尔加成/氮杂傅-克酰基化反应

Scheme 13. Copper/N,O-ligand and BF3?Et2O-catalyzed Michael addition/aza-Friedel-Crafts reaction

图式14. 镍催化的多米诺Heck环化反应

Scheme 14. Nickel-catalyzed domino Heck cyclization reaction

图式15. 铁催化的镁氢化还原环化反应

Scheme 15. Iron-catalyzed reductive cyclization by hydromagnesiation

图式16. 钯催化芳胺取代的炔基环己二酮的不对称环化反应

Scheme 16. Palladium-catalyzed asymmetric cyclization of aniline-tethered alkynyl cyclohexadienones

图式17. 钯催化炔烃合成吲哚衍生物

Scheme 17. Palladium-catalyzed synthesis of indole derivatives from alkynes

图式18. 钯催化合成具有手性C2-芳基轴的吲哚

Scheme 18. Palladium-catalyzed synthesis of indoles bearing a chiral C2-aryl axis

图式19. 钯催化邻碘芳炔酰胺与1,2-二叔丁基二氮杂-3-酮的环化反应

Scheme 19. Palladium-catalyzed cyclization of o-iodoaryna- mide with 1,2-di-tert-butyldiaza-3-one

图式20. 钯催化炔芳基碘与仲羟胺的环化反应

Scheme 20. Palladium-catalyzed cyclization of alkyne aryl iodide with secondary hydroxylamine

图式21. 钯催化炔芳基碘与叔羟胺的环化反应

Scheme 21. Palladium-catalyzed cyclization of alkyne aryl iodide with tert-hydroxylamine

图式22. 钯催化炔基丙二腈氨基环化和不对称腈加成级联反应

Scheme 22. Pd-catalyzed amino-cyclization and desymmetri- zing nitrile addition cascade reaction of alkyne-tethered malononitrile

图式23. 钯催化炔基亲核试剂的多米诺环化反应

Scheme 23. Palladium-catalyzed domino cyclization of alkyne-tethered nucleophiles

图式24. 钌催化N-芳基吡唑酮与内炔的环化反应

Scheme 24. Ruthenium-catalyzed cyclization of N-arylpyrazo- lone with alkyne

图式25. 铑催化N-烷基苯胺与内炔的环化反应

Scheme 25. Rhodium-catalyzed cyclization of N-alkylaniline with endoyne

图式26. 铑催化1-芳基吡唑烷酮与炔基环丁醇的环化反应

Scheme 26. Rhodium-catalyzed cyclization of 1-aryl pyrazolidinone with alkynyl cyclobutanol

图式27. 镍或铜催化合成吲哚衍生物的环化反应

Scheme 27. Nickel- or copper-catalyzed cyclization for the synthesis of indole derivatives

图式28. 金催化去芳构化串联环化反应

Scheme 28. Gold-catalysed dearomative cascade cyclization

图式29. 钯催化邻卤烯酰胺与邻炔基苯胺的Heck环化反应

Scheme 29. Palladium-catalyzed Heck cyclization of o-halogenamide with o-ynylaniline

图式30. 钯催化邻碘烯酰胺与内炔的环化反应

Scheme 30. Palladium-catalyzed cyclization of o-iodoaryna- mide with alkyne

图式31. 具有生物活性的苯并噻吩和苯并噻唑类化合物

Scheme 31. Biologically active benzothiophene and benzothiazole compounds

图式32. 铜催化的交叉偶合反应

Scheme 32. Copper-catalyzed cross-coupling reactions

图式33. 铜催化三组分串联环化合成苯并噻唑

Scheme 33. Copper-catalyzed three-component tandem cyclization for the synthesis of benzothiazole

图式34. 铜催化三组分串联环化合成双硫杂环化合物的反应

Scheme 34. Copper-catalyzed three-component tandem cyclization for the synthesis of bis-thiocyclic compounds

图式35. 铑催化三组分串联环化反应合成苯并噻吩

Scheme 35. Rhodium-catalyzed three-component tandem cyclization for the synthesis of benzothiophene

图式36. 具有生物活性的喹啉类化合物

Scheme 36. Biologically active quinolines

图式37. 钌催化氧化环化反应

Scheme 37. Ruthenium-catalyzed oxidative cyclization reactions

图式38. 钯催化邻甲酰基炔酰胺碳环化反应

Scheme 38. Palladium-catalyzed carbocyclization of o-formylalynamide

图式39. 锌催化合成4-取代喹啉的环化反应

Scheme 39. Zinc-catalyzed cyclization for the synthesis of 4-substituted quinolines

图式40. 钯催化2-叠氮苯基丙炔醇环化反应

Scheme 40. Palladium-catalyzed cyclization of 2-azidophenyl- propynol

图式41. 铜催化芳基腈与2-乙炔芳胺的环化反应

Scheme 41. Copper-catalyzed cyclization of arylonitrile and 2-ethynylaniline

图式42. 铜催化的分子内[4+2]环加成反应

Scheme 42. Copper-catalyzed intramolecular [4+2] cycloaddition reactions

图式43. 铜催化2-芳炔吡啶选择性环化反应

Scheme 43. Copper-catalyzed selective cyclization of 2-aryl pyridine

图式44. 金催化1,8-二炔环异构化反应

Scheme 44. Gold-catalyzed 1,8-diyne isomerization reaction

图式45. 银催化邻炔基芳亚胺与吲哚的串联环化反应

Scheme 45. Silver-catalyzed tandem cyclization of o-alkynyl- aryimine with indole

图式46. 钯催化合成苯并呋喃和吲哚啉衍生物

Scheme 46. Palladium-catalyzed synthesis of benzofuran and indolin derivatives

图式47. 铑催化偶氮苯转化为吲哚和吲哚啉的反应

Scheme 47. Rhodium-catalyzed conversion of azo-benzenes to indoles and indolines

图式48. 钯催化的不对称串联Heck/Suzuki偶联反应

Scheme 48. Palladium-catalyzed asymmetric tandem Heck/ Suzuki coupling reaction

图式49. 钯催化炔烃和2-碘衍生物的偶联-环化反应

Scheme 49. Palladium-catalyzed coupling-cyclization reactions of alkynes and 2-iodo derivatives

图式50. 钯催化三组分串联环化反应

Scheme 50. Palladium-catalyzed three-component cascade cyclization reactions

图式51. 钯催化1,6-烯炔与芳基硼酸和二氟碘乙酸乙酯的串联环化反应

Scheme 51. Palladium-catalyzed cascade cyclization of 1,6-enyne with arylboronic acid and ethyl difluoroiodoacetate

图式52. 镍催化N-(2-溴苯基)-N-丙烯酰胺与三氟甲基烯烃的环化反应

Scheme 52. Nickel-catalyzed cyclization of N-(2-bromophenyl)-N-acrylamide with trifluoromethylolefins

图式53. 钯催化烯丙基醚的多米诺环化反应

Scheme 53. Palladium-catalyzed domino cyclization of allyl ethers

图式54. 银促进烯炔酮与氰基乙酸酯的环化反应

Scheme 54. Silver-promoted cyclization of ene-yne-ketone with cyanoacetate

图式55. 铑催化非定向C—H活化反应

Scheme 55. Rhodium-catalyzed undirected C—H activation reaction

图式56. 纳米钯催化邻碘苄三氮唑与炔烃串联环化反应

Scheme 56. Nanopalladium-catalyzed tandem cyclization of o-iodobenzyltriazole with alkynes

图式57. 铜催化二炔不对称环化反应

Scheme 57. Copper-catalyzed asymmetric cyclization of diynes

图式58. 铜催化称叠氮烯炔的不对称环化反应

Scheme 58. Copper-catalyzed asymmetric cyclization of azide enynes

图式59. 钯催化的Heck环化反应

Scheme 59. Palladium-catalyzed Heck cyclization reaction

图式60. Ni/Al双金属催化烯烃的环化反应

Scheme 60. Ni-Al bimetallic-catalyzed acyclization of olefins

图3. 具有苯并呋喃结构的抗肿瘤剂

Figure 3. Antitumor agent with benzofuran structure

图4. 具有苯并呋喃结构的抗肿瘤剂

Figure 4. Antitumor agent with benzofuran structure

图5. 具有吲哚结构的抗肿瘤剂

Figure 5. Antitumor agent with indole structure

图6. 具有吲哚结构的抗肿瘤剂

Figure 6. Antitumor agent with indole structure

图7. 具有吲哚结构的抗肿瘤剂

Figure 7. Antitumor agent with indole structure

图8. 具有吲哚结构的抗肿瘤剂

Figure 8. Antitumor agent with indole structure

图9. 具有苯并噻唑结构的抗肿瘤剂

Figure 9. Antitumor agents with benzothiazole structure

图10. 具有苯并噻唑结构的抗肿瘤剂

Figure 10. Antitumor agents with benzothiazole structure

图11. 具有苯并噻唑结构的抗肿瘤剂

Figure 11. Antitumor agents with benzothiazole structure

图12. 具有苯并噻唑结构的抗肿瘤剂

Figure 12. Antitumor agents with benzothiazole structure

图13. 具有苯并噻唑结构的抗肿瘤剂

Figure 13. Antitumor agents with benzothiazole structure

图14. 具有喹啉结构的抗肿瘤剂

Figure 14. Antitumor agent with quinoline structure

图15. 具有喹啉结构的抗肿瘤剂

Figure 15. Antitumor agent with quinoline structure

图16. 具有喹啉结构的抗肿瘤剂

Figure 16. Antitumor agent with quinoline structure

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