Design, Synthesis, and Biological Evaluation of Chalcone Derivatives as Novel Anticandidal Agents

Shan, Yuanyuan; Lei, Jin’e; Zhang, Li; Fan, Te; Wang, Maoyi; Ma, Ying

doi:10.1007/s10600-015-1369-6

Cited by 3 publications

(2 citation statements)

References 13 publications

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“…The treatment of CA infections requires addressing both candida virulence traits and antifungal resistance. CA can powerfully switch between budded yeast and filamentous forms (pseudohyphae, true hyphae) in a reversible manner, which contributes to its high pathogenicity in humans by facilitating proliferation and colonization in various tissues through its virulence traits [ 2 , 3 ]. In the immune system, only phagocytic cells can kill Candida in vitro , making the resistance of CA to phagocyte killing a crucial virulence mechanism.…”

Section: Introductionmentioning

confidence: 99%

Plumieride as a novel anti-fungal and anti-inflammatory iridoid against superficial candidiasis in mice

El-Shiekh,

Meselhy,

Elshimy

et al. 2024

BMC Complement Med Ther

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In the past few decades, there has been a notable rise in the occurrence of several types of candidiasis. Candida albicans is the most common cause of superficial fungal infections in humans. In this study, plumieride, one of the major iridoids from Plumeria obtusa L. leaves, was isolated and investigated for its potential against Candida albicans (CA)-induced dermatitis in mice. qRT-PCR was done to assess the impact of plumieride on the expression of the major virulence genes of CA. Five groups (n = 7) of adult male BALB/c mice were categorized into: group I: non-infected mice; group II: mice infected intradermally with 107–108 CFU/mL of CA; group III: CA-infected mice treated with standard fluconazole (50 mg/kg bwt.); group IV and V: CA-infected mice treated with plumieride (25- and 50 mg/kg. bwt., respectively). All the treatments were subcutaneously injected once a day for 3 days. Skin samples were collected on the 4th day post-inoculation to perform pathological, microbial, and molecular studies. The results of the in vitro study proved that plumieride has better antifungal activity than fluconazole, manifested by a wider zone of inhibition and a lower MIC. Plumieride also downregulated the expression of CA virulence genes (ALS1, Plb1, and Hyr1). CA-infected mice showed extensive dermatitis, confirmed by strong iNOS, TNF-α, IL-1β, and NF-κB genes or immune expressions. Whereas the treatment of CA-infected mice with plumieride significantly reduced the microscopic skin lesions and modulated the expression of all measured proinflammatory cytokines and inflammatory markers in a dose-dependent manner. Plumieride interfered with the expression of C. albicans virulence factors and modulated the inflammatory response in the skin of mice infected with CA.

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Section: Introductionmentioning

confidence: 99%

Plumieride as a novel anti-fungal and anti-inflammatory iridoid against superficial candidiasis in mice

El-Shiekh,

Meselhy,

Elshimy

et al. 2024

BMC Complement Med Ther

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“…Method: Adapted from a reported procedure by Ma. 278 To a solution of IV-27 (200 mg, 0.685 mmol) in THF (3 mL) was added distilled H2O (1 mL) and NaH2PO4 (49 mg, 0.41 mmol).…”

Section: Ir (N CMmentioning

confidence: 99%

Síntesis de compuestos aza-bicíclicos por ciclación intramolecular de imidas

Yovanny Quevedo Acosta

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Controlling (E/Z)‐Stereoselectivity of −NHC=O Chlorination: Mechanism Principles for Wide Scope Applications

Maklad,

Moustafa,

Aoyama

et al. 2024

Chemistry A European J

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Organic halogen compounds are cornerstones of applied chemical sciences. Halogen substitution is a smart molecular design strategy adopted to influence reactivity, membrane permeability and receptor interaction. Chiral bioreceptors may restrict the stereochemical requirements in the halo‐ligand design. Straightforward (but expensive) catalyzed stereospecific halogenation has been reported. Historically, PCl5 served access to uncatalyzed stereoselective chlorination although the stereochemical outcomes were influenced by steric parameters. Nonetheless, stereochemical investigation of PCl5 reaction mechanism with carbamoyl (RCONHX) compounds has never been addressed. Herein, we provide the first comprehensive stereochemical mechanistic explanation outlining halogenation of carbamoyl compounds with PCl5; the key regioselectivity‐limiting nitrilimine intermediate (8‐Z.HCl); how substitution pattern influences regioselectivity; why oxadiazole byproduct (P1) is encountered; stereo‐electronic factors influencing the hydrazonoyl chloride (P2) production; and discovery of two stereoselectivity‐limiting parallel mechanisms (stepwise and concerted) of elimination of HCl and POCl3. DFT calculations, synthetic methodology optimization, X‐ray evidence and experimental reaction kinetics study evidence all supported the suggested mechanism proposal (Scheme 2). Finally, we provide mechanism‐inspired future recommendations for directing the reaction stereoselectivity toward elusive and stereochemically inaccessible (E)‐bis‐hydrazonoyl chlorides along with potentially pivotal applications of both (E/Z)‐stereoisomers especially in medicinal chemistry and protein modification.

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Design, Synthesis, and Biological Evaluation of Chalcone Derivatives as Novel Anticandidal Agents

Cited by 3 publications

References 13 publications

Plumieride as a novel anti-fungal and anti-inflammatory iridoid against superficial candidiasis in mice

Plumieride as a novel anti-fungal and anti-inflammatory iridoid against superficial candidiasis in mice

Síntesis de compuestos aza-bicíclicos por ciclación intramolecular de imidas

Controlling (E/Z)‐Stereoselectivity of −NHC=O Chlorination: Mechanism Principles for Wide Scope Applications

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