Synthesis and Antifungal Activity of Novel Chiral <i>α</i>‐Aminophosphonates Containing Fluorine Moiety

Yang, Song; Gao, Xingwen; Diao, Chun-Ling; Song, Baoan; Jin, Linhong; Xu, Guoyong; Zhang, Guoping; Wang, Wei; Hu, Deyu; Xue, Wei; Zhou, Xia; Lü, Ping

doi:10.1002/cjoc.200690296

Cited by 54 publications

(23 citation statements)

References 17 publications

(7 reference statements)

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“…The bioassay results showed that the racemate possessed good antiviral and antitumor activities. [36][37][38][39][40] As different chiral aminophosphonates and their derivatives display varying bioactivities, screening of fluorine derivatives bearing a-amiophosphonate moieties might lead to new antiviral agent with more potent antiviral activities. Keeping these considerations in mind, herein a series of new fluorine containing bioactive chiral a-aminophosphonates were asymmetrically synthesized using chiral Bronsted acid organocatalyst 3 7,41-45 derived from (R)-or (S)-BINOL 46 in a typical hydrophosphonylation reaction of aldimines obtained from cinnamaldehyde and fluorinated aromatic amine with dialkyl phosphites.…”

Section: Introductionmentioning

confidence: 99%

An effective route to fluorine containing asymmetric α‐aminophosphonates using chiral Bronsted acid catalyst

Bhadury

Zhang

et al. 2008

Chirality

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Asymmetric addition of dialkyl phosphites (--CH2CH3, --CH2CH2CH3, --CH(CH3)2, --CH2(CH2)3CH3, --CH2CH2OCH3 and --CH2CH2OC2H5) induced by chiral organocatalyst e.g. (R)- and (S)-3,3'-[3,5-bis(trifluoromethyl)phenyl]2-1,1'-binaphthyl phosphate on fluorinated aldimines derived from cinnamaldehyde has been found effective to give new bioactive alpha-aminophosphonates in good yields (58-73%) and high enantiomeric excess (64.6%-90.6%) under mild conditions.

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Section: Introductionmentioning

confidence: 99%

An effective route to fluorine containing asymmetric α‐aminophosphonates using chiral Bronsted acid catalyst

Bhadury

Zhang

et al. 2008

Chirality

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“…However, the antibacterial activity of α-aminophosphonates has been reported in the literature against gram-positive and gram-negative bacteria, [9][10][11][12] but the new synthesized compounds in this paper had MIC more than 256 µg/ ml against the investigated bacteria. It has been reported that pharmacological effects of α-aminophosphonates are sterospecific; [8] therefore, we suggest that antibacterial effect of these compounds may be stereoselective and the antibacterial evaluation of each enantiomer separately can confirm this matter.…”

Section: Antimicrobial Assaymentioning

confidence: 75%

“…[1][2][3][4][5] It has been reported that some alkyl-substituted phosphonate compounds have antifungal activity, [7,8] antibacterial activity, [9][10][11][12] antitumor effects [13][14][15] and antiviral activity. [16] Also, the activities of α-aminophosphonates as peptidomimetics, [17] enzyme inhibitors, [18] haptens of catalytic antibodies, [19] herbicidals, [20] inhibitors of serine hydrolases [21] and inhibitors of UDP-galactopyranose mutase [22] are reported in literature.…”

Section: Introductionmentioning

confidence: 99%

Design and one-pot synthesis of new α-aminophosphonates and antimicrobial activity

Rezaei

Khabnadideh

Ghasemi

et al. 2011

J Pharm Negative Results

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Background: α-Aminophosphonates are bioisosters of amino acids and have several pharmacological effects. α-Aminophosphonates have been synthesized by various routes from reaction between an amine, an aldehyde, and phosphate compounds. Materials and Methods: We synthesized 20 new α-aminophosphonates in the presence of FeCl3 in THF as a catalyst to facilitate the Manich-type reaction of aldehyde, amine and phosphite compounds to form the corresponding α-aminophosphonates in a one-pot, three-component reaction. In this study, the catalytic effect of ZnCl2 was also compared with FeCl3 in the synthesis of α-aminophosphonates. Results: The results showed that FeCl3 catalyzed the reaction in mild conditions to form α-aminophosphonates with high yields, but ZnCl2 did not give high yields of the compounds and the reaction took longer time in comparison to that taken by FeCl3 The chemical structures of all new compounds were confirmed by spectrophotometric methods (1HNMR, 13CNMR, IR). The compounds were investigated for antimicrobial activity against Escherichia coli, Bacillus subtilis, Salmonella typhi, Shigella sonnei, Proteus vulgaris, and Staphylococcus epidermidis. Conclusion: The new synthesized compounds did not show good antibacterial activity against the tested microorganisms

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“…100 µg/mL) was added to sterilized Czapek media (0.2 % NaNO 3 , 0.131 % K 2 HPO 4 ·3H 2 O, 0.05 % KCl, 0.05 % MgSO 4 ·7H 2 O, 0.00183 % FeSO 4 ·7H 2 O, 3 % sucrose, pH 6.8) [17] in which F. oxysporum had incubated for a few days. After incubating together at 27 o C for 24 h, it was observed under microscope (Olympus 800 ×).…”

Section: Hyphal Morphology Of F Oxysporummentioning

confidence: 99%

Synthesis, Antiviral and Antifungal Bioactivity of 2-Cyano-acrylate Derivatives Containing Phosphonyl Moieties

Wang

Song

et al. 2007

Molecules

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Alkyl 2-cyano-3-methylthio-3-phosphonylacrylates were synthesized by the reaction of alkyl 2-cyano-3,3-dimethylthioacrylates with dialkyl phosphites. The structures of the new compounds were characterized by elemental analyses, IR, 1 H-, 13 C-and 31 P-NMR spectral data. These compounds were tested in vitro against pathogenic fungi, namely, Fusarium graminearum, Cytospora mandshurica and Fusarium oxysporum. Amongst all compounds, 2d and 2t were found to be effective against the tested fungi at 50 µg/mL. A half-leaf method was used to determine the in vivo protective, inactivation and curative efficacies of the title products against tobacco mosaic virus (TMV). Title compounds 2a and 2b were found to possess good in vivo curative, protection and inactivation effects against TMV with inhibitory rates at 500 mg/L of 60.0, 89.4 and 56.5 and 64.2, 84.2 and 61.2 %, respectively. To the best of our knowledge, this is the first report on the antiviral and antifungal activity of alkyl 2-cyano-3-methylthio-3-phosphonylacrylates.

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Synthesis and Antifungal Activity of Novel Chiral α‐Aminophosphonates Containing Fluorine Moiety

Cited by 54 publications

References 17 publications

An effective route to fluorine containing asymmetric α‐aminophosphonates using chiral Bronsted acid catalyst

An effective route to fluorine containing asymmetric α‐aminophosphonates using chiral Bronsted acid catalyst

Design and one-pot synthesis of new α-aminophosphonates and antimicrobial activity

Synthesis, Antiviral and Antifungal Bioactivity of 2-Cyano-acrylate Derivatives Containing Phosphonyl Moieties

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