Nội dung được dịch bởi AI, chỉ mang tính chất tham khảo
Tổng hợp các dimethylmaleimide chứa N-substituted và hoạt tính chống nấm của chúng đối với Sclerotinia sclerotiorum
Tóm tắt
Các hợp chất chứa maleimide, cả tự nhiên và tổng hợp, có hoạt tính sinh học tốt, đặc biệt là hoạt tính chống nấm. Để điều tra hoạt tính chống nấm của các dimethylmaleimide, 17 dimethylmaleimide chứa N-substituted đã được chuẩn bị từ phản ứng của 2,3-dimethylmaleic anhydride và amin bằng phương pháp tổng hợp đơn giản trong bài báo này. Các hợp chất này đã được đánh giá về hoạt tính chống nấm đối với Sclerotinia sclerotiorum bằng phương pháp đo tốc độ sinh trưởng mycelium. Chúng thể hiện nồng độ ức chế tối thiểu (MIC) dao động từ 0.01–50.0 μg/mL, trong đó N-(2-benzimidazole)-3,4-dimethylmaleimide là hoạt chất mạnh nhất với MIC là 0.01 μg/mL. Mối quan hệ giữa cấu trúc và hoạt tính của những hợp chất này chỉ ra rằng tính kỵ nước của các nhóm N-substituents có liên quan đến hoạt tính chống nấm của chúng. So với các thuốc chống nấm hiện tại, hầu hết các dimethylmaleimide chứa N-substituted có hoạt tính tuyệt vời để kiểm soát S. sclerotiorum và độc tính thấp.
Từ khóa
#dimethylmaleimide #N-substituted #hoạt tính chống nấm #Sclerotinia sclerotiorum #nồng độ ức chế tối thiểu (MIC)Tài liệu tham khảo
Ahemad M, Khan MS (2012) Biotoxic impact of fungicides on plant growth promoting activities of phosphate-solubilizing Klebsiella sp isolated from mustard (Brassica campestris) rhizosphere. J Pest Sci 85:29–36
Amri I, Gargouri S, Lamia Hamrouni L, Hanana M, Fezzani T, Jamoussi B (2012) Chemical composition, phytotoxic and antifungal activities of Pinus pinea essential oil. J Pest Sci 85:199–207
Chen XL, Zheng YG, Shen YC (2007) Natural products with maleic anhydride structure: nonadrides, tautomycin, chaetomellic anhydride and other compounds. Chem Rev 107:1777–1830
Chen XL, Xu YH, Zheng YG, Shen YC (2010) Improvement of tautomycin production in Streptomyces spiroverticillatus by feeding glucose and maleic anhydride. Biotechnol Bioprocess Eng 15:969–974
Chen XL, Zhu XH, Ding YC, Shen YC (2011) Antifungal activity of tautomycin and related compounds against Sclerotinia sclerotiorum. J Antibiot 64:563–569
Daniela I, Mircea C (2003) Computational study of maleamic acid cyclodehydration. J Phys Org Chem 16:348–354
David C, Emmanuelle SS (2010) Monohalogenated maleimides as potential agents for the inhibition of Pseudomonas aeruginosa biofilm. Biofouling 26:379–385
Denicola SA, Anderson BM (1990) Nonpolar interactions in the maleimide inactivation of Haemophilus influenzae D-lactate dehydrogenase. BBA Protein Struct M 1040:84–88
Frederic Z, Alain V (2002) Synthesis and antimicrobial activities of N-substituted imides. IL Farmaco 57:421–426
Jens RA, Irma KB, Beata AC, Anthony CWA, Edward HD, Stephen SB, Edward TC, Vito FD (2005) The synthesis and biological evaluation of two analogues of the C-riboside showdomycin. Aust J Chem 58:86–93
Jerzy K (2003) Synthesis of new N-substituted cyclic imides with potential anxiolytic activity. Xxv. Derivatives of halogenodibenzo (e.h) bicyclo(2.2.2) otcane- 2,3-dicarboximide. Acta Pol Pharm 60:1183–1189
Jiang L, Liu F, Zhang DK, Wang HB (2010) Synthesis and antifungal activity of 1-substitutedphenyl-3-(5-halobenzimidazol-2-yl) acylurea. J Pest Sci 35:33–35
Juerg K, Theobaid H et al. (1984) Process for preparing N-substituted dimethylmaleimides. CH 641161 (A5)
Khan MI, Baloch MK, Ashfaq M (2004) Biological aspects of new organotin (IV) compounds of 3-maleimidopropionic acid. J Organomet Chem 689:3370–3378
Li W, Fan YX, Shen ZZ, Chen XL, Shen YC (2012) Antifungal activity of simple compounds with maleic anhydride or dimethylmaleimide structure against Botrytis cinerea. J Pest Sci 37:1–5
Manas KS, Debjani D, Dulal P (2006) Pyrene excimer fluorescence of yeast alcohol dehydrogenase: a sensitive probe to investigate ligand binding and unfolding pathway of the enzyme. Photochem Photobiol 82:480–486
Marcus EB, Hans B, Werner B, Grety R, Tammo W (1984) Mechanismus der decarboxylativen dimerisierung von maleinsaureanhydrid zu dimethyl malein saure anhydrid unter einfluss von 2-aminopyridin. Helv Chim Acta 67:1897–1905
Nara LM, Gislaine F, Carla S (2010) N-antipyrine-3,4-dichloromaleimide, an effective cyclic imide for the treatment of chronic pain: the role of the glutamatergic system. Anesth Analg 110(3):942–950
Natalia S, Joanna BM et al (2011) Chemical reactivity and antimicrobial activity of N-substituted maleimides. J Enzyme Inhib Med Chem 27:117–124
Ohta H, Suzuki S, Watanabe H, Jikihara T, Matsuya K, Wakabayashi K (1976) Structure-activity relationship of cyclic imide herbicides. I. N-substituted phenyl-3,4,5,6-tetrahydrophthalimides and related compounds. Agric Biol Chem 40:745–751
Rheinfelden NB, Basel MB, Riehen DB, Aesch ES (1982) Cyclobutanedicarboxylic acid imides, and compositions for their use as phytopathogenic fungicides. US Patent 4361576
Sauers CK, Middlebush (1962) Preparation of maleimides. US Patent 3018290
Seyran M, Brenneman TB, Stevenson KL (2010) In vitro toxicity of alternative oxidase inhibitors salicylhydroxamic acid and propyl gallate on Fusicladium effusum. J Pest Sci 83:421–427
Silvia NL, Maria VC et al (2005) In vitro antifungal properties, structure-activity relationships and studies on the mode of action of N-phenyl, N-aryl, N-phenylalkyl maleimides and related compounds. Arzneim-Forsch 55:123–132
Slavica A, Dib I, Nidetzky B (2007) Selective modification of surface-exposed thiol groups in Trigonopsis variabilis D-amino acid oxidase using poly (ethylene glycol) maleimide and its effect on activity and stability of the enzyme. Biotechnol Bioeng 96:9–17
Sortino M, Garibotto F, Cecheinel FV, Gupta M, Enriz R, Zacchino S (2011) Antifungal, cytotoxic and SAR studies of a series of N-alkyl, N-aryl and N-alkylphenyl-1,4-pyrrolediones and related compounds. Bioorg Med Chem 19:2823–2834
Sosabowski JK, Matzow T, Foster JM, Finucane C, Ellison D, Watson SA, Mather SJ (2009) Targeting of CCK-2 receptor-expressing tumors using a radiolabelled divalent gastrin peptide. J Nucl Med 50:2082–2089
Sudisha J, Niranjana SR, Sukanya SL, Girijamba R, Lakshmi Devi N, Shekar Shetty H (2010) Relative efficacy of strobilurin formulations in the control of downy mildew of sunflower. J Pest Sci 83:461–470
Sunita RD, Shailaji PM, Anjali PL, Preeti MC (2010) A facile synthesis of N-substituted maleimides. Indian J Chem Sect B 49:487–488
Tang CC, Li YX, Chen B, Yang HZ, Jin GY (1998) Fungicide in pesticide chemistry. Nankai University Press, Nanjing, pp 342–345
Thomas B, Stephan AS (2010) Showdomycin as a versatile chemical tool for the detection of pathogenesis-associated enzymes in bacteria. J Am Chem Soc 132:6964–6872
Torigaoka TY (1986) A process for producing N -substituted maleimides. EP 0177031A1
Tsou KC, Barrnentt RJ (1955) Preparation of some N-(1-naphthyl)-maleimides as sulfhydryl group reagents. J Am Chem Soc 77:4613–4616
Wael AZ, Clarisse BF, Fondja Y (2010) Aqabamycins A-G: novel nitro maleimides from a marine Vibrio species: I. taxonomy, fermentation, isolation and biological activities. J Antibiot 63:297–301
Watanabe S, Igarashi Y, Yagami K (1992) Antimicrobial activity of some N-(arylalkyl)-maleimides. J Pest Sci 34:99–104
Wu MD, Cheng MJ (2008) Maleimide and maleic anhydride derivatives from the mycelia of Antrodia cinnamomea and their nitric oxide inhibitory activities in macrophages. J Nat Prod 71:1258–1261
Wu P, Hu YZ (2009) Synthesis of novel 1,4-benzoxazine-2,3-dicarboximides from maleic anhydride and substituted aromatic amines. Synth Commun 39:70–84
Yu XY, Corten C, Gornerc H, Wolff T, Kuckling D (2008) Photodimers of N-alkyl-3,4-dimethylmaleimides-product ratios and reaction mechanism. J Photochem Photobiol A 198:34–44
Zicmanis A, Hamaide T, Graillat C, Monnet C, Abele S, Guyot A (1997) Synthesis of new alkyl maleates ammonium derivatives and their uses in emulsion polymerization. Colloid Polym Sci 275:1–8