69906-04-3Relevant articles and documents
Diastereoselective Synthesis of Novel Pyrrolidine or Pyrrolizine-Fused Benzo-δ-sultams via 1,3-Dipolar Cycloadditions
Ghandi, Mehdi,Kia, Maryam Asle,Sadeghzadegh, Masoud,Bozcheloei, Abolfazl Hasani,Kubicki, Maciej
, p. 1646 - 1653 (2015)
The synthesis of novel pyrrolidine or pyrrolizine-fused benzosultams is described. A number of (E)-N-(2-formylphenyl)-N-alkyl-2-phenylethenesulfonamides derivatives were synthesized and subjected to intramolecular [3+2] cycloaddition with azomethine ylides derived in situ from the reaction with sarcosine, phenylglycine, and L-proline.
Design, Synthesis, and Antifungal Evaluation of Neocryptolepine Derivatives against Phytopathogenic Fungi
Gao, Jian-Mei,Lawoe, Raymond Kobla,Liu, Ying-Qian,Shang, Xiao-Fei,Sun, Yu,Yang, Cheng-Jie,Yin, Xiao-Dan,Zhao, Zhong-Min,Zhou, Rui,Zhu, Jia-Kai
, p. 2306 - 2315 (2020/03/10)
Neocryptolepine is an alkaloid isolated from traditional African herbal medicine Cryptolepis sanguinolenta, and its broad spectrum of biological activities has been illuminated in past decades. In this study, neocryptolepine and its derivatives (1-49) were designed and synthesized from economical and readily available starting materials. Their structures were confirmed by proton nuclear magnetic resonance, carbon nuclear magnetic resonance, and mass spectrometry. The synthesized compounds were screened for their antifungal profile against six agriculturally important fungi Rhizoctonia solani, Botrytis cinerea (B. cinerea), Fusarium graminearum, Mycosphaerella melonis, Sclerotinia sclerotiorum, and Magnaporthe oryzae. The results of in vitro assay revealed that compounds 5, 21, 24, 35, 40, 45, and 47 presented remarkable antifungal activity against the fungi tested with EC50 values lower than 1 μg/mL. Significantly, compound 24 displayed the most effective inhibitory potency against B. cinerea (EC50 = 0.07 μg/mL), and the data from in vivo experiments revealed that compound 24 demonstrated comparable protective activity with the positive control boscalid. Preliminary mechanism studies indicated that compound 24 showed impressive spore germination inhibitory effectiveness and lower cytotoxicity than azoxystrobin, imparted on normal function of the cell membrane and cell wall, and arrested the normal function of the nucleus. Besides the excellent inhibitory activity against agriculturally important phytopathogenic fungi tested, the designed assemblage possesses several benefits with a high profile of variation in synthesized molecules, the ease of synthesis, and good cost-effectiveness of commercially available synthetic reagents, all of these have highlighted the potential worth of compound 24 as a new and highly efficient agricultural fungicide.
Expedient synthesis of novel coumarin-based sulfonamides
Ghandi, Mehdi,Babazadeh, Elham
, p. 379 - 387 (2015/02/05)
The synthesis of novel coumarin-based sulfonamides was accomplished in good yields via InCl3-catalyzed three-component condensation of N-(2-formylphenyl)-N-methylbenzenesulfonamides, 4-hydroxycoumarin and cyclic secondary amines in toluene.
Synthesis of novel tetra- and pentacyclic benzosultam scaffolds via domino Knoevenagel hetero-Diels-Alder reactions in water
Ghandi, Mehdi,Sheibani, Shahab,Sadeghzadeh, Masoud,Daha, Fariba Johari,Kubicki, MacIej
, p. 1057 - 1065 (2013/11/06)
An efficient catalyst-free and diastereoselective synthesis of novel dihydropyrano[2,3-d]pyrimidine and dihydropyrano[3,2-c]chromen-annulated benzosultams is described. A number of (E)-N-(2-formylphenyl)-N-methyl-2- phenylethenesulfonamides were synthesized and underwent a one-pot domino Knoevenagel hetero-Diels-Alder reaction, respectively, with N,N- dimethylbarbituric acid and 4-hydroxycoumarin in water, giving the desired products, in moderate to excellent yields.
