127793-64-0Relevant academic research and scientific papers
Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations
Beattie, Ryan J.,Hornsby, Thomas W.,Craig, Gemma,Galan, M. Carmen,Willis, Christine L.
, p. 2743 - 2747 (2016)
A de novo approach for the rapid construction of orthogonally protected l- and d-deoxysugars and analogues is described. A novel and robust silicon-acetal undergoes Prins cyclisations with a series of homoallylic alcohols in high yield and excellent stereocontrol. Modified Tamao-Fleming oxidation of the resulting silyltetrahydropyrans gives direct access to deoxyglycoside analogues and the approach was showcased in the synthesis of protected l-oliose, a component of the anticancer agent aclacinomycin A.
Scalable Synthesis of l - Allo -Enduracididine: The Unusual Amino Acid Present in Teixobactin
Gangathade, Namdeo,Nayani, Kiranmai,Bukya, Hemalatha,Mainkar, Prathama S.,Chandrasekhar, Srivari
, p. 1465 - 1468 (2021/07/14)
A scalable synthesis of l - allo -enduracididine is achieved from commercially available (S)-glycidol in ten linear steps involving well-established synthetic transformations. The synthetic route is flexible and can be used to synthesize all four diastere
Total Synthesis of Citreochlorol Monochloro Analogues via a Catalytically Enantioselective Carbonyl Allylation
Hsieh, Bing-Han,Lin, Cheng-Kun,Wu, Chun-Fu
, (2021/11/22)
An efficient synthetic route to citreochlorol analogues, halogenated polyketide secondary metabolites, is described. The key features are Krische s enantioselective carbonyl allylation, IBr-promoted cyclization, and regioselective epoxide opening. The importance of the route lies in accessing a versatile epoxy ether that enables the formation of citreochlorol monochloro derivatives.
COMPOUNDS AND METHODS FOR THE TREATMENT OF PARASITIC DISEASES
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, (2018/10/19)
Provided herein are compounds useful for the treatment of various parasitic diseases. These compounds, as well as pharmaceutically acceptable salts thereof may be formulated in pharmaceutical compostions, veterinary compositions and may be used in methods
(-)-Tarchonanthuslactone: Design of New Analogues, Evaluation of their Antiproliferative Activity on Cancer Cell Lines, and Preliminary Mechanistic Studies
Toneto Novaes, Luiz Fernando,Martins Avila, Carolina,Pelizzaro-Rocha, Karin Juliane,Vendramini-Costa, Débora Barbosa,Pereira Dias, Marina,Barbosa Trivella, Daniela Barreto,Ernesto De Carvalho, Jo?o,Ferreira-Halder, Carmen Veríssima,Pilli, Ronaldo Aloise
, p. 1687 - 1699 (2015/10/06)
Natural products containing the α,β-unsaturated δ-lactone skeleton have been shown to possess a variety of biological activities. The natural product (-)-tarchonanthuslactone (1) possessing this privileged scaffold is a popular synthetic target, but its biological activity remains underexplored. Herein, the total syntheses of dihydropyran-2-ones modeled on the structure of 1 were undertaken. These compounds were obtained in overall yields of 17-21 % based on the Keck asymmetric allylation reaction and were evaluated in vitro against eight different cultured human tumor cell lines. We further conducted initial investigation into the mechanism of action of selected analogues. Dihydropyran-2-one 8 [(S,E)-(6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl 3-(3,4-dihydroxyphenyl)acrylate], a simplified analogue of (-)-tarchonanthuslactone (1) bearing an additional electrophilic site and a catechol system, was the most cytotoxic and selective compound against six of the eight cancer cell lines analyzed, including the pancreatic cancer cell line. Preliminary studies on the mechanism of action of compound 8 on pancreatic cancer demonstrated that apoptotic cell death takes place mediated by an increase in the level of reactive oxygen species. It appears as though compound 8, possessing two Michael acceptors and a catechol system, may be a promising scaffold for the selective killing of cancer cells, and thus, it deserves further investigation to determine its potential for cancer therapy. Fighting the big C: We describe the synthesis of a new family of analogues based on the scaffold of the natural product (-)-tarchonanthuslactone; these compounds were evaluated in vitro against tumor cell lines. We further conducted an initial investigation into the mechanism of action, including the inhibition of phosphatases and glutathione-S-transferase and the production of reactive oxygen species.
ARYL FUSED LACTAMS AS EZH2 MODULATORS
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, (2016/04/19)
This invention relates to compounds of Formula (I) in which R1, R2, R3, R4, X and Z are as defined herein, and the pharmaceutically acceptable salts thereof, to pharmaceutical compositions comprising such compounds and salts, and to methods of using such compounds, salts and compositions for the treatment of abnormal cell growth, including cancer.
Stereoselective synthesis of the C1-C12 subunit of (-)-callystatin A
Raghavan, Sadagopan,Rajendar, Sheelamanthula
supporting information, p. 4371 - 4373 (2015/06/22)
A stereoselective synthesis of the C1-C12 fragment of callystatin A is disclosed. The two stereocenters at C5 and C10 were created by an organocatalytic reaction and a diastereoselective alkylation, respectively. The trisubstituted double bond was introdu
Coibacins a and b: Total synthesis and stereochemical revision
Carneiro, Vania M. T.,Avila, Carolina M.,Balunas, Marcy J.,Gerwick, William H.,Pilli, Ronaldo A.
, p. 630 - 642 (2014/04/03)
The interface between synthetic organic chemistry and natural products was explored in order to unravel the structure of coibacin A, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp. that exhibits selective antileishmanial activity and potent antiinflammatory properties. Our synthetic plan focused on a convergent strategy that allows rapid access to the desired target by coupling of three key fragments involving E-selective Wittig and modified Julia olefinations. CD measurements and comparative HPLC analyses of the natural product and four synthetic stereoisomers led to determination of its absolute configuration, thus correcting the original assignment at C-5 and unambiguously establishing those at C-16 and C-18. Additionally, we synthesized coibacin B on the basis of the assignment of configuration for coibacin A.
ARYL AND HETEROARYL FUSED LACTAMS
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, (2014/07/08)
This invention relates to compounds of general formula (I) in which R1, R2, U, V, L, M, R5, m, X, Y and Z are as defined herein, and the pharmaceutically acceptable salts thereof, to pharmaceutical compositions comprising such compounds and salts, and to methods of using such compounds, salts and compositions for the treatment of abnormal cell growth, including cancer.
Concise synthesis of acetal-protected syn 1,3-diols by a tandem hemiacetal formation/Tsuji-Trost reaction
Wang, Liang,Menche, Dirk
supporting information, p. 9425 - 9427 (2012/10/30)
Designed, developed, and applied: A novel domino sequence was used for the rapid assembly of acetal-protected syn 1,3-diols. The convergent synthesis of a polyol fragment of the macrolide antibiotic RK-397 demonstrates that this method is suitable for the rapid and stereoselective preparation of polyketide-type diol motifs.
