Discovery of inhibitors of brassinin oxidase based on the scaffolds of the phytoalexins brassilexin and wasalexin

Pathogen inactivation of cruciferous phytoalexins: detoxification reactions, enzymes and inhibitors

“…32 In vitro screening of this synthetic library using puried BOLm indicated that none of the synthetic compounds were inhibitory to BOLm, but demonstrated for the rst time that the phytoalexins camalexin (35) and cyclobrassinin (12) were competitive inhibitors of BOLm. 27 Later on, compounds with scaffolds based on various phytoalexins (Table 1), including camalexin (35) 33 and brassilexin (20), 34 were shown to inhibit BOLm. 6-Chlorobrassilexin (74) and 5-methoxycamalexin (66) were determined to be the best competitive inhibitors of BOLm to date (Table 1).…”

“…6-Chlorobrassilexin (74) and 5-methoxycamalexin (66) were determined to be the best competitive inhibitors of BOLm to date (Table 1). 34 However, due to their substantial antifungal activity against L. maculans, these inhibitors are not considered paldoxins. This antifungal activity is not surprising considering that the designed inhibitor structures were based on phytoalexins.…”

Inhibitors of the Detoxifying Enzyme of the Phytoalexin Brassinin Based on Quinoline and Isoquinoline Scaffolds

“…As part of a research program to devise sustainable methods to protect plants against fungal infections, we are particularly interested in the development of paldoxins, i.e., phytoalexin detoxification inhibitors [ 4 ]. Paldoxins of BOLm [ 5 , 6 ] are being considered as potential crop protectants having a specific mechanism of action, the inhibition of brassinin detoxification by L. maculans [ 7 ]. The attraction of this approach lies in the possibility of exploiting paldoxins as selective fungal enzyme inhibitors.…”

A Versatile Approach for the Synthesis of 8H‐Thieno[2,3‐b]indoles and N‐[2‐(2‐N‐(R1,R2)‐2‐Thioxoacetyl)‐phenyl]acetamides from 1‐Acetyl‐1,2‐dihydro‐3H‐indol‐3‐one (Acetylindoxyl) and Its Derivatives: A Novel Synthesis of Intermediate (1‐Acetyl‐1H‐indol‐3‐yl)malononitrile/cyanoacetates

“…In the course of our ongoing studies of the chemical and biological properties of linear hetero[b]fused indoles [1][2][3][4], we have developed effective and simple methods for the synthesis of pharmacologically interesting pyridazino [4,3b]indoles [5], pyrano [3,2-b]indoles [6], pyrrolo [3,2-b] indoles [7], imidazo [4,5-b]indoles, thiazolo [5,4-b]indoles [8], and some of their analogs [9,10]. A number of representatives of these series displayed antituberculosis, monoamine oxidase inhibiting, antiviral, antihypoxic, and hepatoprotective activities some of which may be attributable to monoamine oxidase inhibition.…”

“…In particular, thienodolin (6-chlorothieno [2,3-b]indole-2-carboxamide) isolated from the culture broth of Streptomyces albogriseolus [3] and characterized by Japanese researches has proved to have plant-growth-regulation activity. The parent thieno [2,3-b]indole also demonstrated antifungal activity [4]. Several syntheses of thieno [2,3-b]indoles have been reported, some in recent years [19][20][21][22][23][24].…”