吩嗪-1-羧酸及其类似物研究进展

doi:10.6023/cjoc201904023

摘要/Abstract

吩嗪-1-羧酸是一种广泛存在于假单胞菌和链霉菌等微生物的次级代谢产物, 对植物病原菌具有很好的抑制活性, 同时兼具医用杀菌及抗肿瘤等活性. 综述了吩嗪-1-羧酸的生物合成与化学合成, 并对目前吩嗪-1-羧酸天然类似物以及化学合成类似物的生物活性研究进行了总结, 为此类化合物的结构改造与活性研究提供参考.

关键词: 吩嗪-1-羧酸, 类似物, 研究进展

Phenazine-1-carboxylic acid (PCA) as a natural product widely exists in microbial metabolites of Pseudomonads and Streptomycetes, which displays potent inhibitory activities against plant pathogens, and has medical antibacterial and antitumor effects, and so on. In this review, the biosynthesis and chemosynthesis of phenazine-1-carboxylic acid are summarized. At the same time, the diverse biological evaluations of its biosynthetic and chemosynthetic analogues are summarized, which could provide reference for the study of structural modifications and biological activities of these analogues.

Key words: phenazine-1-carboxylic acid, analogues, research progress

引用此文

朱祥, 吴清来, 李俊凯. 吩嗪-1-羧酸及其类似物研究进展[J]. 有机化学, 2019, 39(10): 2744-2758.

Zhu Xiang, Wu Qinglai, Li Junkai. Research Progress of Phenazine-1-carboxylic Acid and Its Analogue[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2744-2758.

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图/表 31

图1. 吩嗪-1-羧酸的化学结构

Figure 1. Chemical structure of phenazine-1-carboxylic acid

图2. 吩嗪-1-羧酸和吩嗪-1,6-二羧酸的生物合成

Figure 2. Biosynthesis of phenazine-1-carboxylic scid and phenazine-1,6-dicarboxylic acid

图3. 吩嗪类似物的生物合成

Figure 3. Biosynthesis of derivatives of phenazine

图式1. 邻氨基苯甲酸与硝基苯反应

Scheme 1. Reaction of o-aminobenzoic acid with nitrobenzene

图式2. 邻苯二胺与1-甲基-2,3-二羟基环己烯反应

Scheme 2. Reaction of o-phenylenediamine with 1-methyl-2,3- dihydroxy cyclohexene

图式3. 2,3-二氨基苯甲酸与1,2-环己二酮反应

Scheme 3. Reaction of 2,3-diaminobenzoic acid with 1,2-cyclo- hexanedione

图式4. 3-甲基邻苯二胺与邻苯二酚反应

Scheme 4. Reaction of 3-methylbenzene-1,2-diamine with pyrocatechol

图式5. 吩嗪-1-甲基与NBS反应生成吩嗪-1-羧酸

Scheme 5. Reaction of phenazine-1-methyl with NBS to phenazine-1-carboxylic acid

图式6. 以3-硝基苯胺为原料合成吩嗪-1-羧酸

Scheme 6. Synthesis of phenazine-1-carboxylic acid from 3- nitroaniline

图式7. 铜催化2-溴-3-硝基苯甲酸与苯胺的Jourdan-Ullmann偶联反应

Scheme 7. Cu-catalyzed Jourdan-Ullmann reaction of 2-bromo- 3-nitrobenzoic acid with aniline

图式8. 钯催化邻溴硝基苯与苯胺偶联反应

Scheme 8. Pd-catalyzed ullmann-coupling of o-bromonitro- benzene with aniline

图式9. Benzoxepine-4-carboxylates与苯二胺反应

Scheme 9. Reaction of Benzoxepine-4-carboxylates with benzene-1,2-diamine

图式10. 以dibenzodiazepines为底物合成吩嗪

Scheme 10. Synthesis of phenazines from dibenzodiazepines

Compd.	R¹	R²	R³	R⁴	R⁵	R⁶	R⁷	R⁸
1	OH	H	H	H	H	H	H	H
2	NH₂	H	H	H	H	H	H	H
3	NHNH₂	H	H	H	H	H	H	H
4	OH	OH	H	H	H	H	H	H
5	OH	H	H	OH	H	H	H	H
6	OH	H	H	H	OH	H	H	H
7	OH	H	H	H	H	H	H	OH
8	OH	OH	OH	H	H	H	H	H
9	OH	OH	H	H	OH	H	H	H
10	OH	OH	H	H	H	H	H	OH
11	OH	OH	OH	OH	H	H	H	H
12	OH	H	H	H	COOH	H	H	H
13	OH	OH	OH	H	COOH	H	H	H
14	OCH₃	H	H	H	COOCH₃	OH	H	H
15	OCH₃	H	H	OH	COOCH₃		H	H
16	OCH₃	H	H	OH	COOCH₃		H	OH
17	OH	OCH₃	H	H	H		H	H

表1. 由假单胞菌产生的简单PCA衍生物

Table 1. Simple derivatives of PCA produced by pseudomona s

Compd.	R¹	R²	R³	R⁴	R⁵	R⁶	R⁷	R⁸
20	OH	H	OH	H	OH	H	H	H
21	OH	H	H	H	CH₂OH	H	H	OH
22	OH	H	H	H	CH₃	H	H	OCH₃
23	OH	H	H	H	COOCH₃	H	H	H
24	OH	OH	H	H	COOCH₃	H	H	H
25	OCH₃	H	H	H		H	H	H
26	OCH₃	H	H	H	OCH₃	H	H	H

表2. 由链霉菌产生的简单PCA衍生物

Table 2. Simple derivatives of PCA produced by Streptomyces

图式11. 吩嗪-1-酰胺52的合成

Scheme 11. Synthesis of phenazine-1-carboxamides 52

图式12. 吩嗪-1-酰胺53的合成

Scheme 12. Synthesis of phenazine-1-carboxamides 53

图式13. 双吩嗪-1-酰胺54的合成

Scheme 13. Synthesis of bis(phenazine-1-carboxamides) 54

图式14. 苯并吩嗪-6-酰胺55的合成

Scheme 14. Synthesis of benzo[a]-phenazine-6-carboxamides 55

图式15. 吩嗪-1-酰胺63的合成

Scheme 15. Synthesis of phenazine-1-carboxamides 63

图式16. 氨基吩嗪-1-羧酸酯64、65的合成

Scheme 16. Synthesis of aminophenazine-1- carboxylates 64 and 65

图式17. 吩嗪-1-酰胺66的合成

Scheme 17. Synthesis of phenazine-1-carboxamides 66

图式18. 基于羧基改造的吩嗪-1-羧酸衍生物的合成

Scheme 18. Synthesis of Phenazine-1-carboxylic acid derivatives based on the modification of PCA carboxyl group

图式19. 吩嗪-1-羧酸双酰肼衍生物的合成

Scheme 19. Synthesis of phenazine-1-carboxylic acid diacylhydrazine derivatives

图式20. 吩嗪-1-酰胺衍生物的合成

Scheme 20. Synthesis of phenazine-1-carboxylic acid diacylhydrazine derivatives

图式21. 吩嗪-1-羧酸双酰胺衍生物的合成

Scheme 21. Synthesis of phenazine-1-carboxylic acid diamide derivatives

图式22. 吩嗪-1-羧酸1,3,4-恶二唑硫醚衍生物的合成

Scheme 22. Synthesis of phenazine-1-carboxylic acid 1,3,4- oxadiazol-2-yl thioether derivatives of phenazine-1-carboxylic acid

图式23. 吩嗪-1-羧酸水杨酸酯衍生物

Scheme 23. Phenazine-1-carboxylic acid-hydroxybenzoic acid ester derivatives

图式24. 吩嗪-1-羧酸哌嗪衍生物的合成

Scheme 24. Synthesis of phenazine-1-carboxylic-piperazine derivatives

Compd.	EC₅₀/(μmol?L^–1)
Compd.	Rhizoctonia solani	Alternaria solani	Fusarium oxysporu	Fusarium graminearum	Pyricularia oryzac Cavgra
86a	24.6±0.8	42.9±2.1	73.7±1.6	73.8±2.2	34.2±3.3
PCA	33.2±2.3	81.5±4.3	186.5±1.2	176.4±2.1	37.3±1.9

表3. 化合物86a和申嗪霉素对5种病原真菌的离体杀菌活性

Table 3. Fungicidal activities of 86a and PCA against five pathogenic fungi in vitro

图式25. 吩嗪-1-羧酸-L-丙氨酸耦合物的合成

Scheme 25. Synthesis of phenazine-1-carboxylic-L-alanine conjugates

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