137571-75-6Relevant academic research and scientific papers
Synthetic cajaninstilbene acid derivatives eradicate methicillin-resistant Staphylococcus aureus persisters and biofilms
Chen, Wei-Min,Hou, Wen,Huang, Mei-Yan,Lin, Jing,Meng, Ying,Xu, Xiao-Fang,Yu, Jia-Hui
, (2021/07/22)
The Staphylococcus aureus can switch to a transient genotype-invariant dormancy, known as a persister, to survive treatment with high doses of antibiotics. This transient persister is an important reason underlying its resistance. There is an urgent need to find new antibacterial agents capable of eradicating methicillin-resistant S. aureus (MRSA) persisters. In this study, 37 new derivatives of cajaninstilbene acid (CSA) were designed and synthesized, and their biological activity against MRSA persisters was evaluated. Most of the newly synthesized derivatives exhibit more potent antimicrobial properties against S. aureus and MRSA than CSA itself, and 23 of the 37 derivatives show a tendency to eradicate MRSA persisters. A representative compound (A6) was demonstrated to target bacterial cell membranes. It eradicated the adherent biofilm of MRSA in a concentration dependent manner, and showed a synergistic antibacterial effect with piperacilin. In a model mouse abscess caused by MRSA persisters, A6 effectively reduced the bacterial load in vivo. These results indicate that A6 is a potential candidate for treatment of MRSA persister infections.
First Total Synthesis of Gaylussacin and Its Stilbene Derivatives
Song, Injae,Lim, Hyewon,Chun, Simin,Lee, Seok Beom,Huh, Jungmoo,Oh, Dong-Chan,Hong, Suckchang
supporting information, p. 1366 - 1372 (2021/04/09)
Gaylussacin (1), a stilbene glucoside, has been isolated fromPentarhizidium orientaleand is used in Korean folk medicine. Although it was first isolated in 1972, the synthesis of gaylussacin has never been reported. Herein, we report the first total synth
Total synthesis and structural revision of greensporone F and dechlorogreensporone F
Mohapatra, Debendra K.,Gaddam, Janardhan,Reddy, Aedula Vishnu V.,Sarma, Akella V.S.,Yadav, Jhillu S.
, p. 12418 - 12429 (2020/11/10)
The first asymmetric total syntheses of the real isolation product (2S,5R,8R)-greensporone F and (2S,5R,8R)-dechlorogreensporone F, 14-membered resorcylic acid lactones with a cis-2,5-disubstituted tetrahydrofuran ring system, was accomplished. The synthesis features a late-stage Lewis acid-catalyzed stereoselective intramolecular oxa-Michael reaction, E-selective ring-closing metathesis, De Brabander's esterification, and Jacobsen's hydrolytic kinetic resolution as the key steps. Synthesis of both real isolation and erroneously proposed structure necessitated the revision of the absolute configuration of greensporone F and dechlorogreensporone F. The erroneous representation of (2S,5S,8S)-configuration in greensporone F and dechlorogreensporone F was assigned to be (2S,5R,8R) by comparison with the NMR data and specific rotation of the synthetic compounds with that of the reported data.
A convergent approach toward fidaxomicin: Syntheses of the fully glycosylated northern and southern fragments
De Brabander, Jef K.,Hollibaugh, Ryan,Yu, Xueliang
supporting information, (2020/10/27)
Efficient approaches that enable the synthesis of analogs of natural product antibiotics are needed to keep up with the emergence of multiply-resistant strains of pathogenic organisms. One promising candidate in this area is fidaxomicin, which boasts impressive in vitro anti-tubercular activity but has poor systemic bioavailability. We designed a flexible synthetic route to this target to enable the exploration of new chemical space and the future development of analogs with superior pharmacokinetics. We developed a robust approach to each of the key macrocyclic and sugar fragments, their union via stereoselective glycosylation, and a convergent late-stage macrolide formation with fully glycosylated fragments. Although we were able to demonstrate that the final Suzuki cross-coupling and ring-closing metathesis steps enabled macrocycle formation in the presence of the northern resorcylic rhamnoside and southern novioside sugars, these final steps were hampered by poor yields and the formation of the unwanted Z-macrocycle as the major stereoisomer.
Total synthesis and stereochemical revision of relgro and 10′-oxorelgro
Gaddam, Janardhan,Reddy, G. Sudhakar,Marumudi, Kanakaraju,Kunwar, Ajit C.,Yadav, Jhillu S.,Mohapatra, Debendra K.
, p. 5601 - 5614 (2019/06/13)
The first asymmetric total synthesis and stereochemical assignments of 10-membered macrolactones relgro and 10′-oxorelgro are disclosed. To this end, palladium-catalyzed Stille coupling, the Mitsunobu reaction, ring-closing metathesis, EDCI promoted coupling and the Jacobsen hydrolytic kinetic resolution are used as key steps. The total synthesis followed by thorough evaluation of the optical rotation and CD spectral data led to the revision of the absolute configuration at C-6′ for both relgro and 10′-oxorelgro. Moreover, the 1H as well as 13C NMR data are reported for the first time for relgro.
Total Synthesis and Structural Revision of Monocillin VII
Mallampudi, N. Arjunreddy,Srinivas, Beduru,Reddy, Jithender G.,Mohapatra, Debendra K.
supporting information, p. 5952 - 5956 (2019/08/26)
The first asymmetric total synthesis of macrolactone monocillin VII and its C-10′ epimer was achieved starting from a known chiral pure epoxide in 16 longest linear sequences. The present synthesis highlights the macrolactone formation involving an alkyne-dicobalt carbonyl complex under De Brabander's conditions followed by an unexpected regioselective hydration. The asymmetric total synthesis resulted in the revision of the configuration at C10′ and reassignment of the absolute configuration of the natural product.
Synthetic process for natural product Amorfrutin C with anticancer activity
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Paragraph 0020; 0040-0042, (2019/01/07)
The invention relates to the synthesis of natural products, especially to a synthetic process for the natural product Amorfrutin C with anticancer activity, belonging to the technical fields of chemical organic synthesis and pharmacy. According to the invention, the compound 2,4,6-trihydroxybenzoic acid is used as a starting material; a phenethyl side chain is introduced through a suzuki reaction;a diisopentenyl side chain is introduced through NaH-mediated [1,1]-rearrangement; altogether eight steps of reactions are carried out to complete the synthesis of Amorfrutin C, and gram-level scale-up can be realized; and a water-sensitive cyclization step in the prior art is avoiding, so a foundation is laid for the smooth realization of the full synthesis and industrial production of Amorfrutin C. A plurality of structural sites of the natural product Amorfrutin C with anticancer activity are modified in the invention; high yield is realized; and the synthetic process is suitable for pilotscale-up and subsequent industrialization, so mass chemical synthesis of the natural product and its derivatives can be realized.
Gold(I)-Catalyzed Cyclization for the Synthesis of 8-Hydroxy-3- substituted Isocoumarins: Total Synthesis of Exserolide F
Mallampudi, N. Arjunreddy,Reddy, G. Sudhakar,Maity, Saurabh,Mohapatra, Debendra K.
supporting information, p. 2074 - 2077 (2017/04/28)
A highly regioselective gold(I)-catalyzed 6-endo-dig cyclization of 2,2-dimethyl-5-(alkynyl)-4H-benzo[d][1,3]dioxin-4-ones for the synthesis of 8-hydroxy-3-substituted isocoumarins is described. Key features of the reaction include the broad substrate scope, scalability, and tolerance for protecting groups. The synthetic utility of this novel method is demonstrated by the first total synthesis of exserolide F, an isocoumarin-containing polyol natural product.
Stereoselective synthesis of (3R,6S)-6-hydroxylasiodiplodin
Bujaranipalli, Sheshurao,Das, Saibal
supporting information, p. 1653 - 1655 (2016/04/04)
The first stereoselective synthesis of polyketide natural product (3R,6S)-6-hydroxylasiodiplodin (1) has been described starting from commonly available starting materials d-mannitol and 2,4,6-trihydroxybenzoic acid. The key reactions involved are Keck asymmetric allylation, Stille coupling, De Brabander's esterification, and ring-closing metathesis (RCM) reaction. The total synthesis was achieved in 19.3% overall yield making the route significant.
Revision of the structure and total synthesis of altenuisol
Nemecek, Gregor,Cudaj, Judith,Podlech, Joachim
scheme or table, p. 3863 - 3870 (2012/09/25)
A total synthesis of the reported structure of altenuisol is described. Comparison of the 1H NMR spectra of the synthesized compound and of the natural product revealed that the originally proposed structure was not correct. Consequently, two constitutional isomers were synthesized. The spectra of one of these compounds - a structure originally proposed as the structure of altertenuol - matched perfectly with the spectra of the natural product. The total synthesis of altenuisol was thus achieved starting with phloroglucinic acid and protocatechuic aldehyde in 10 steps and in 23% yield, where the longest linear sequence consisted of 6 steps. The key step was a Suzuki coupling with concomitant formation of the lactone ring. Whether altertenuol is identical with altenuisol could not be decided. Total synthesis of altenuisol, a minor toxin in ubiquitous Alternaria spp. revealed that the originally proposed structure was not correct. Altenuisol was proved to have an isomeric structure by total synthesis. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
