66696-84-2Relevant academic research and scientific papers
A donor-acceptor cyclopropene as a dipole source for a silver(i) catalyzed asymmetric catalytic [3+3]-cycloaddition with nitrones
Xu, Xinfang,Zavalij, Peter J.,Doyle, Michael P.
, p. 10287 - 10289 (2013)
Silver(i)-catalyzed asymmetric formal [3+3]-cycloaddition of nitrones with a donor-acceptor cyclopropene, formed in situ from dirhodium acetate-catalyzed dinitrogen extrusion/intramolecular cyclization of enoldiazoacetates, effectively generates 3,6-dihydro-1,2-oxazine derivatives in high yield and with exceptional stereocontrol.
Isolation of N-(2-Methyl-3-oxodecanoyl)pyrrole and N-(2-Methyl-3-oxodec-8-enoyl)pyrrole, Two New Natural Products from Penicillium brevicompactum, and Synthesis of Analogues with Insecticidal and Fungicidal Activity
Canti?n, A?ngel,Moya, Pilar,Miranda, Miguel A.,Primo, Jaime,Primo-Y?fera, Eduardo
, p. 4748 - 4753 (1998)
Two new natural products have been isolated from culture broth of Penicillium brevicompactum Dierckx. The structures have been assigned as N-(2-methyl-3-oxodecanoyl) pyrrole and N-(2-methyl-3-oxodec-8-enoyl)pyrrole on the basis of spectral data. Synthesis of analogues has been carried out by acylation of the pyrrole ring at C2 with different acylated Meldrum's acids. Two analogues (6b and 7b) have shown interesting insecticidal activities, and three other ones (6a, 6c, and 7a) have exhibited significant broad-spectrum fungicidal activities. These synthetic products might be considered as a starting point in the search for new pesticides.
5-Carbonyl-1,3-oxazine-2,4-diones from N-Cyanosulfoximines and Meldrum's Acid Derivatives
Brosge, Felix,Kochs, Johannes Florian,Bregu, Mariela,Truong, Khai-Nghi,Rissanen, Kari,Bolm, Carsten
supporting information, p. 6667 - 6670 (2020/09/02)
At elevated temperatures, N-cyanosulfoximines react with Meldrum's acid derivatives to give sulfoximines with N-bound 5-carbonyl-1,3-oxazine-2,4-dione groups. A representative product was characterized by single-crystal X-ray structure analysis. The product formation involves an unexpected molecular reorientation requiring several sequential bond-forming and-cleaving processes.
Expanded Structure-Activity Studies of Lipoxazolidinone Antibiotics
Mills, Jonathan J.,Pierce, Joshua G.,Robinson, Kaylib R.
supporting information, p. 374 - 377 (2019/03/21)
The lipoxazolidinone family of marine natural products, which contains an unusual 4-oxazolidinone core, was found to possess potent antimicrobial activity against methicillin resistant Staphylococcus aureus (MRSA). Herein, we expanded our previous synthet
Enantioselective Carbene Cascade: An Effective Approach to Cyclopentadienes and Applications in Diels–Alder Reactions
Wang, Xiangbo,Zhou, Yunfei,Qiu, Lihua,Yao, Ruwei,Zheng, Yang,Zhang, Cheng,Bao, Xiaoguang,Xu, Xinfang
supporting information, p. 1571 - 1576 (2016/10/13)
An asymmetric carbene cascade reaction, which proceeds through carbene/alkyne metathesis and formal (3+2) cycloaddition and converts alkynyl-tethered enol diazoacetates to chiral bicyclic cyclopentadienes, is presented; and no catalytic asymmetric version of these carbene cascade transformations has been disclosed so far. The proton signals of the cyclopropene intermediates are observed in the mechanism study, which clearly demonstrate the reaction pathways. In addition, these products are intercepted via Diels–Alder reactions to provide bridged polycyclic structures in high yields and enantioselectivities. (Figure presented.).
Structure Property Relationships of Carboxylic Acid Isosteres
Lassalas, Pierrik,Gay, Bryant,Lasfargeas, Caroline,James, Michael J.,Tran, Van,Vijayendran, Krishna G.,Brunden, Kurt R.,Kozlowski, Marisa C.,Thomas, Craig J.,Smith, Amos B.,Huryn, Donna M.,Ballatore, Carlo
, p. 3183 - 3203 (2016/05/19)
The replacement of a carboxylic acid with a surrogate structure, or (bio)-isostere, is a classical strategy in medicinal chemistry. The general underlying principle is that by maintaining the features of the carboxylic acid critical for biological activity, but appropriately modifying the physicochemical properties, improved analogs may result. In this context, a systematic assessment of the physicochemical properties of carboxylic acid isosteres would be desirable to enable more informed decisions of potential replacements to be used for analog design. Herein we report the structure-property relationships (SPR) of 35 phenylpropionic acid derivatives, in which the carboxylic acid moiety is replaced with a series of known isosteres. The data set generated provides an assessment of the relative impact on the physicochemical properties that these replacements may have compared to the carboxylic acid analog. As such, this study presents a framework for how to rationally apply isosteric replacements of the carboxylic acid functional group.
Practical, asymmetric route to sitagliptin and derivatives: Development and origin of diastereoselectivity
Gutierrez, Osvaldo,Metil, Dattatray,Dwivedi, Namrata,Gudimalla, Nagaraju,Chandrashekar,Dahanukar, Vilas H.,Bhattacharya, Apurba,Bandichhor, Rakeshwar,Kozlowski, Marisa C.
supporting information, p. 1742 - 1745 (2015/04/14)
The development of a practical and scalable process for the asymmetric synthesis of sitagliptin is reported. Density functional theory calculations reveal that two noncovalent interactions are responsible for the high diastereoselection. The first is an intramolecular hydrogen bond between the enamide NH and the boryl mesylate S=O, consistent with MsOH being crucial for high selectivity. The second is a novel C-H···F interaction between the aryl C5-fluoride and the methyl of the mesylate ligand.
Synthesis and biological evaluation of novel 2-Arylalkylthio-5-iodine-6- substituted-benzyl-pyrimidine-4(3H)-ones as Potent HIV-1 Non-Nucleoside reverse transcriptase inhibitors
Zhang, Liang,Tang, Xiaowan,Cao, Yuanyuan,Wu, Shaotong,Zhang, Yu,Zhao, Jianxiong,Guo, Ying,Tian, Chao,Zhang, Zhili,Liu, Junyi,Wang, Xiaowei
, p. 7104 - 7121 (2014/07/08)
A novel series of 2-arylalkylthio-5-iodine-6-substitutedbenzyl-pyrimidine- 4(3H)- ones (S-DABOs) 8a-x had been synthesized via an efficient method. Their biological activity against HIV virus and RT assay were evaluated. Some compounds, especially 8h, 8l and 8n, displayed promising activity against HIV-1 RT with IC50 values in a range of 0.41 μM to 0.71 iM, which were much better than that of nevirapine. Molecular modeling studies revealed that the binding mode would be affected via forming an additional hydrogen bond by incorporating an oxygen atom on the C-2 side chain. The biological activity was in accordance with the docking results.
Bioisosteric replacement of an acylureido moiety attached to an indolin-2-one scaffold with a malonamido or a 2/4-pyridinoylamido moiety produces a selectively potent Aurora-B inhibitor
Wang, Hsiao-Chun,Jagtap, Ajit Dhananjay,Chang, Pei-Teh,Liu, Jia-Rong,Liu, Chih-Peng,Tseng, Hsiang-Wen,Chen, Grace Shiahuy,Chern, Ji-Wang
, p. 312 - 334 (2014/08/05)
Bioisosteric replacement of acylureido moiety in 6-acylureido-3- pyrrolylmethylidene-2-oxoindoline derivatives resulted in a series of malonamido derivatives with indolin-2-one scaffold (11-14). Further conformational restrictions of the malonamido moiety led to 2-oxo-1,2-dihydropyridine (21-25) or a 4-oxo-1,4-dihydropyridine derivatives (31-36). 4-Oxo-1,4-dihydropyridine derivatives were more potent Aurora B inhibitors than their 2-oxo-1,2- dihydropyridine counterparts and demonstrated cytotoxicities against A549 and HepG2 cells in the submicromolar range. In A549 cells, 31h decreased phosphorylation of histone H3, triggered polyploidy, induced expression of pro-apoptotic Fas and FasL with subsequent activation of caspase 8, resulting into apoptosis. In a Huh7-xenograft mouse model, 31h demonstrated potent in vivo efficacy with a daily dose of 5 mg/kg.
Creation through immobilization: A new family of high performance heterogeneous bifunctional iminophosphorane (BIMP) superbase organocatalysts
Goldys, Anna M.,Nez, Marta G.,Dixon, Darren J.
supporting information, p. 6294 - 6297 (2015/02/05)
An immobilized chiral bifunctional iminophosphorane superbase organocatalyst has been developed and applied in a range of challenging enantioselective reactions. A unique feature of this novel catalytic system is that the final step creation of the iminophosphorane occurs at the point of immobilization. The utility of the immobilized catalyst system was demonstrated in the nitro-Mannich reaction of ketimines as well as the conjugate addition of high pKa 1,3-dicarbonyl pro-nucleophiles to nitrostyrene. Catalyst recycling was also demonstrated.
