Synthesis of novel triazole derivatives as potent inhibitor of allene oxide synthase (CYP74A), a key enzyme in jasmonic acid biosynthesis

Oh, Keimei; Nakai, Kouta; Yamada, Keiko; Yoshizawa, Yuko

doi:10.1584/jpestics.d11-006

Cited by 8 publications

(3 citation statements)

References 23 publications

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“…The intermediate 2‐bromo‐1‐phenylenthanone ( 2 ) was synthesized from acetophenone ( 1 ) by reacting with bromine in liquid phase using aluminum chloride as catalyst in ice bath . Then, ( 2 ) was submitted to 1,2,4‐triazole and trimethylamine to obtain the 1‐phenyl‐2‐(1 H ‐1,2,4‐triazol‐1‐yl)ethanone ( 3 ) . The 2‐bromo‐1‐phenyl‐2‐bromo‐(1 H ‐1,2,4‐triazol‐1‐yl)ethanone ( 4 ) can be obtained by bromination of 1‐phenyl‐2‐(1H‐1,2,4‐triazol‐1‐yl)ethanone ( 3 ) reacting with liquid bromine with anhydrous sodium acetate and glacial acetic acid .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Novel 2‐Substituted Phenoxy‐N‐(4‐substituted Phenyl‐5‐(1H‐1,2,4‐triazol‐1‐yl)thiazol‐2‐yl)acetamide Derivatives

Liao

Zhou

Xiao

et al. 2016

Journal of Heterocyclic Chem

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A series of 2‐substituted phenoxy‐N‐(4‐substituted phenyl‐5‐(1H‐1,2,4‐triazol‐1‐yl)thiazole‐2‐yl)acetamide derivatives 8a, 8b, 8c, 8d, 8e, 8f, 8g, 8h, 8i, 8j, 8k, 8l, 8m, 8n, 8o, 8p, 8q, 8r, 8s, 8t was synthesized by the reaction of phenoxyacetyl chloride 7 with intermediate 4‐substituted phenyl‐5‐(1H‐1,2,4‐triazol‐1‐yl)thiazol‐2‐amine 5. Their structures were confirmed by 1H NMR, 13C NMR, MS, IR, and elemental analyses. The synthesized compounds were also screened for their antimicrobial activity against three types of plant fungi (Gibberella zeae, Phytophthora infestans, and Paralepetopsis sasakii) and two kinds of bacteria [Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac)] showing promising results. In particular, 8b, 8f, 8g, and 8h exhibited excellent antibacterial activity against Xoo, with 50% effective concentration (EC50) values of 35.2, 80.1, 62.5, and 82.1 µg/mL, respectively, which are superior to the commercial antibacterial agent bismerthiazol (89.9 µg/mL). The preliminary structure–activity relationship studies of these compounds are also briefly described.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Novel 2‐Substituted Phenoxy‐N‐(4‐substituted Phenyl‐5‐(1H‐1,2,4‐triazol‐1‐yl)thiazol‐2‐yl)acetamide Derivatives

Liao

Zhou

Xiao

et al. 2016

Journal of Heterocyclic Chem

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“…Experimental data have been obtained from the literature. [2,7,14] Computationally obtained data for compounds 3a-d are given in Tables 3, 4, 5 and 6. In order to express the agreement between experimental and computationally obtained data, a color scale from red to green has been applied to Tables 3, 4, 5 and 6.…”

Section: Nmr Spectral Analysismentioning

confidence: 99%

“…[1] In most commercially available azoles such as, clotrimazole, miconazole, econazole, oxiconazole etc, gem-phenyl-(1H-imidazol-1-ylmethyl) group is thought to be responsible for the biological activity ( Figure 1). [2] In literature, the synthesis of substituted 1phenylethanone derivatives via the reaction of 2bromoacetophenone with various azole derivatives such as imidazole, [1,3,4] benzimidazole, [2,3,5] 1,2,4triazole [1,[6][7][8] and benzotriazole [3,9,10] have been reported.…”

Section: Introductionmentioning

confidence: 99%

A Computational Study on the Nucleophilic Substitution Reaction between 2-Bromoacetophenone and Azole Derivatives

Erdoğan

2018

Celal Bayar Üniversitesi Fen Bilimleri Dergisi

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In this study, it was aimed to investigate the reaction of 2-bromoacetophenone with various azole derivatives, such as imidazole, benzimidazole, 1,2,4-triazole and benzotriazole computationally. For this purpose, some Density Functional Theory (DFT) calculations have been carried out on the reactants and products at B3LYP (Becke, three-parameter, Lee-Yang-Parr) level of theory using various basis sets, including 6-31G(d), 6-31G(d,p), 6-311G(d,p) and 6-311+G(2d,p). Geometry optimizations, Single Point Energy (SPE) calculations, frequency analysis, frontier molecular orbital calculations, molecular electrostatic potential (MEP) map calculations, and determination of global reactivity descriptors have been carried out at the same levels of theory. In NMR calculations, both Continuous Set of Gauge Transformations (CSGT) and Gauge-Independent Atomic Orbital (GIAO) methods have been used and computationally obtained data have been compared with the experimental data.

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A Three‐Step Chemoenzymatic Cascade Synthesis of Miconazole Analogues Based on the Asymmetric Synthesis of β‐Heteroaryl Amino Alcohols via Ketoreductases

Fang,

Xu,

Ren

et al. 2023

Adv Synth Catal

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Chiral β‐heteroaryl amino alcohols play a crucial role as intermediates in the synthesis of numerous bioactive pharmaceuticals, including cenobamate, oteseconazole, and miconazole. Nevertheless, there is a lack of literature documenting the establishment of a versatile approach for the synthesis of β‐heteroaryl amino alcohols and the aforementioned drugs. In this study, we successfully asymmetrically synthesized 50 pairs of chiral β‐heteroaryl amino alcohols using two engineered ketoreductases (KREDs) with opposite stereopreference. Based on this achievement, we developed a three‐step chemoenzymatic cascade route for synthesizing of chiral miconazole analogues from commercially available 2‐bromoacetophenone derivatives. By optimizing the solvent for the synthesis of α‐imidazolyl ketones in the first step, followed by the reduction of α‐imidazolyl ketones using KREDs in the second step and etherification in the third step, we obtained 20 chiral miconazole analogues with promising yields (26–84%) and impressive stereoselectivities (up to >99% ee). Notably, this route eliminates the need for the isolation of ketone and alcohol intermediates, and avoids the use of metal catalysts in the synthesis of chiral miconazole analogues. Furthermore, we successfully scaled up the preparation of (S)‐miconazole, achieving a 30% isolated yield and >99% ee. This method presents a novel synthetic approach for production chiral ether drugs and chiral β‐heteroaryl amino alcohols, offering new possibilities in pharmaceutical synthesis.

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Synthesis of novel triazole derivatives as potent inhibitor of allene oxide synthase (CYP74A), a key enzyme in jasmonic acid biosynthesis

Cited by 8 publications

References 23 publications

Synthesis and Antimicrobial Activity of Novel 2‐Substituted Phenoxy‐N‐(4‐substituted Phenyl‐5‐(1H‐1,2,4‐triazol‐1‐yl)thiazol‐2‐yl)acetamide Derivatives

Synthesis and Antimicrobial Activity of Novel 2‐Substituted Phenoxy‐N‐(4‐substituted Phenyl‐5‐(1H‐1,2,4‐triazol‐1‐yl)thiazol‐2‐yl)acetamide Derivatives

A Computational Study on the Nucleophilic Substitution Reaction between 2-Bromoacetophenone and Azole Derivatives

A Three‐Step Chemoenzymatic Cascade Synthesis of Miconazole Analogues Based on the Asymmetric Synthesis of β‐Heteroaryl Amino Alcohols via Ketoreductases

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