Synthesis of Azabicyclo[3.1.0]amine Analogues of Anacardic Acid as Potent Antibacterial Agents

Vempati, Ravi Kumar; Reddy, Narra Srikanth; Alapati, Srinivasa Rao; Dubey, P.K.

doi:10.14233/ajchem.2013.13338

Cited by 3 publications

(2 citation statements)

References 12 publications

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“…A series of benzyl amine derivatives of anacardic acid ( 18a – v ) [ 59 ] have been developed ( Figure 6 ) from anacardic acids and assayed for activity against both gram-negative ( E. coli and P. aeruginosa ) and gram-positive bacteria ( S. aureus and S. pyogens ) and compared with standard ampicillin, chloramphenicol, ciprofloxacin, and norfloxacin [ 59 ]. The results revealed that none of the synthesized anacardic acids was superior to standard antibiotics against all tested bacteria.…”

Section: Anacardic Acids As Synthons For Synthesis Of Biologicallymentioning

confidence: 99%

Potential Biological Applications of Bio-Based Anacardic Acids and Their Derivatives

Hamad

Mubofu

2015

IJMS

115

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Cashew nut shells (CNS), which are agro wastes from cashew nut processing factories, have proven to be among the most versatile bio-based renewable materials in the search for functional materials and chemicals from renewable resources. CNS are produced in the cashew nut processing process as waste, but they contain cashew nut shell liquid (CNSL) up to about 30–35 wt. % of the nut shell weight depending on the method of extraction. CNSL is a mixture of anacardic acid, cardanol, cardol, and methyl cardol, and the structures of these phenols offer opportunities for the development of diverse products. For anacardic acid, the combination of phenolic, carboxylic, and a 15-carbon alkyl side chain functional group makes it attractive in biological applications or as a synthon for the synthesis of a multitude of bioactive compounds. Anacardic acid, which is about 65% of a CNSL mixture, can be extracted from the agro waste. This shows that CNS waste can be used to extract useful chemicals and thus provide alternative green sources of chemicals, apart from relying only on the otherwise declining petroleum based sources. This paper reviews the potential of anacardic acids and their semi-synthetic derivatives for antibacterial, antitumor, and antioxidant activities. The review focuses on natural anacardic acids from CNS and other plants and their semi-synthetic derivatives as possible lead compounds in medicine. In addition, the use of anacardic acid as a starting material for the synthesis of various biologically active compounds and complexes is reported.

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Section: Anacardic Acids As Synthons For Synthesis Of Biologicallymentioning

confidence: 99%

Potential Biological Applications of Bio-Based Anacardic Acids and Their Derivatives

Hamad

Mubofu

2015

IJMS

115

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“…Occasionally, the same conversion starting from enyne analogues has also been achieved by a photocatalytic pathway [34][35][36] as well as metal-free organocatalytic processes [37][38][39][40][41][42], mechanisms that are similar to the metal carbene processes (Scheme 1a). Another two effective approaches for the synthesis of 3-azabicyclo[3.1.0]hexanes involve the derivatization reactions of substituted cyclopropanes, such as C(sp 3 )-H bond activated alkenylation/amination tandem reactions and intramolecular aminolysis reactions Molecules 2023, 28, 3691 2 of 15 (Scheme 1b) [43][44][45][46][47][48][49][50][51][52][53], and the reaction of functionalized maleimide derivatives with one carbon donor generated in situ derived from substituted diazomethanes, bromo(nitro)methane, substituted α-diazoacetates, and N-tosylhydrazones via an intermolecular [2+1] fusedannulation reaction (Scheme 1c) [54][55][56][57][58][59][60][61][62][63][64]. In particular, the base-induced intramolecular spirocyclization method of the alkylation subunit precursor appeared to be a more efficient proprietary reaction to access 3-azabicyclo[3.1.0]hexane scaffold-containing natural products via aryl metal or radical dearomatization/cyclization reactions (Scheme 1d) [65][66][67][68][69][70][71]…”

Section: Introductionmentioning

confidence: 99%

Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles

Zhang

Chen

et al. 2023

Molecules

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3-Azabicyclo[3.1.0]hexanes are common structural components in natural products and bioactive compounds. Traditionally, the metal-mediated cyclopropanation domino reaction of chain enzymes is the most commonly used strategy for the construction of this type of aza[3.1.0]bicycle derivative. In this study, a base-promoted intramolecular addition of alkenes used to deliver conformationally restricted highly substituted aza[3.1.0]bicycles is reported. This reaction was tailor-made for saturated aza[3.1.0] bicycle-containing fused bicyclic compounds that may be applied in the development of concise and divergent total syntheses of bioactive compounds.

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Practical Synthesis of a 6-Triazolylazabicyclo[3.1.0]hexane

Sirois¹,

Xu²,

Angelaud³

et al. 2018

Org. Process Res. Dev.

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We describe a practical, scalable synthesis of an advanced heterocyclic intermediate, (1R,5S,6s)-6-(4H-1,2,4-triazol-4-yl)-3-azabicyclo[3.1.0]hexane. A robust synthetic sequence based on a Kulinkovich–de Meijere pyrroline cyclopropanation followed by transamination of N,N′-dimethylformamide azine with the resultant amine was developed to supply >18 kg of the target triazolyl azabicycle with 98 wt % purity in its free base form. Reaction conditions and isolation methods for the key 1,2,4-triazole formation step were explored to minimize undesired reaction pathways and to increase the purity of the product. Additionally, at several stages different freebasing methods were implemented that addressed the high water solubility of the associated nitrogen-rich compounds.

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Synthesis of Azabicyclo[3.1.0]amine Analogues of Anacardic Acid as Potent Antibacterial Agents

Cited by 3 publications

References 12 publications

Potential Biological Applications of Bio-Based Anacardic Acids and Their Derivatives

Potential Biological Applications of Bio-Based Anacardic Acids and Their Derivatives

Base-Promoted Intramolecular Addition of Vinyl Cyclopropanecarboxamides to Access Conformationally Restricted Aza[3.1.0]bicycles

Practical Synthesis of a 6-Triazolylazabicyclo[3.1.0]hexane

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