220231-01-6Relevant academic research and scientific papers
Design and synthesis of 3,4-diarylpyrrole analogues as potent topoisomerase inhibitors
Chen, Wang,Feng, Zili,He, Xu,Zhao, Qiang,Liang, Qi
, p. 485 - 494 (2018/07/25)
Background: The natural products containing a common 3,4-diarylpyrrole skeleton have attracted considerable attention due to their unique structures and multiplex biological activities. In our previous study, lycogarubin C was synthesized and showed cytot
The application of formyl group activation of bromopyrrole esters to formal syntheses of lycogarubin C, permethyl storniamide A and lamellarin G trimethyl ether
Gupton, John T.,Telang, Nakul,Patteson, Jon,Lescalleet, Kristin,Yeudall, Scott,Sobieski, John,Harrison, Andrew,Curry, Will
, p. 9759 - 9767 (2015/01/09)
Lycogarubin C, permethyl storniamide A, and lamellarin G trimethyl ether are pyrrole containing, natural products, which exhibit interesting biological properties. Such properties include anti-tumor activity on a variety of cancer cell lines including those that confer drug resistance, inhibition of HIV integrase, and vascular disrupting activity. We now describe the use of methyl and ethyl 3-bromo-2-formylpyrrole-5-carboxylate as building blocks for the formal synthesis of these three highly functionalized, bioactive pyrroles. These new building blocks will now provide ready access to the natural products and many novel analogs due to the ability to easily modify positions 2,3,4, and 5 of the pyrrole core.
Cu/Mn Co-oxidized cyclization for the synthesis of highly substituted pyrrole derivatives from amino acid esters: A strategy for the biomimetic syntheses of lycogarubin c and chromopyrrolic acid
Zhou, Nini,Xie, Tao,Liu, Lin,Xie, Zhixiang
, p. 6061 - 6068 (2014/07/21)
An effective and concise approach to synthesis of tetrasubstituted pyrroles from readily available amino acid esters by the promotion of Cu(OAc) 2 in conjunction with Mn(OAc)3 has been developed. This reaction proceeds through multiple dehydrogenations, deamination, and oxidative cyclization. This oxidized system tolerates substrates bearing various electron-donating or electron-withdrawing groups. With this methodology, several key intermediates of natural products have been effectively prepared, and the total syntheses of lycogarubin C and chromopyrrolic acid have been completed in high efficiency.
A novel method for the synthesis of 3,4-disubstitutedpyrrole-2,5- dicarboxylates from hydrazones derived from α-diazo esters
Yasui, Eiko,Wada, Masao,Nagumo, Shinji,Takamura, Norio
, p. 4325 - 4330 (2013/06/27)
Hydrazones obtained from α-diazo esters were converted to pyrroles when heated with thionyl chloride in alcohol. Among hydrazones, those substituted with a benzene ring on the β-carbon to the ester are likely to give pyrroles in good yields.
Development of novel pyrrole synthesis for the preparation of intermediates of bioactive pyrrole alkaloids
Yasui, Eiko,Wada, Masao,Takamura, Norio
, p. 4762 - 4765 (2011/03/18)
We have developed a novel method for the synthesis of 3,4-diarylpyrrole-2,5-dicarboxylates via α-diazo esters, which are easily obtained from phenylalanine derivatives. Utilizing this method, intermediates of bioactive compounds having the structure of 3,
A general method for the synthesis of N-unsubstituted 3,4-diarylpyrrole-2, 5-dicarboxylates
Fukuda, Tsutomu,Hayashida, Yukie,Iwao, Masatomo
experimental part, p. 1105 - 1122 (2010/09/16)
A general method for the synthesis of N-unsubstituted 3,4-diarylpyrrole-2, 5-dicarboxylates (3) has been developed. The key reactions involved are the Hinsberg-type synthesis of dimethyl N-benzyl-3,4-dihydroxypyrrole-2,5- dicarboxylate (6) followed by palladium-catalyzed Suzuki-Miyaura coupling of its bis-triflate derivative (7). The N-benzyl protecting group of the resulting 3,4-diaryl pyrrole-2,5-dicarboxyl ates (8) is cleanly removed under hydrogenolytic or solvolytic conditions.
The application of vinylogous iminium salt derivatives and microwave accelerated Vilsmeier-Haack reactions to efficient relay syntheses of the polycitone and storniamide natural products
Gupton, John T.,Banner, Edith J.,Sartin, Melissa D.,Coppock, Matthew B.,Hempel, Jonathan E.,Kharlamova, Anastasia,Fisher, Daniel C.,Giglio, Ben C.,Smith, Kristin L.,Keough, Matt J.,Smith, Timothy M.,Kanters, Rene P.F.,Dominey, Raymond N.,Sikorski, James A.
, p. 5246 - 5253 (2008/09/21)
Studies directed at the synthesis of polycitone and storniamide natural products via vinylogous iminium salts and microwave accelerated Vilsmeier-Haack formylations are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole or a 2,3,4-trisubstituted pyrrole from a vinamidinium salt or vinamidinium salt derivative followed by formylation at the 5-position of the pyrrole. Subsequent transformations of the selectively formylated pyrroles lead to efficient and regiocontrolled relay syntheses of the respective pyrrole containing natural products.
Efficient relay syntheses and assessment of the DNA-cleaving properties of the pyrrole alkaloid derivatives permethyl storniamide A, lycogalic acid A dimethyl ester, and the halitulin core
Fürstner, Alois,Krause, Helga,Thiel, Oliver R
, p. 6373 - 6380 (2007/10/03)
Palladium catalyzed Suzuki- and Negishi cross coupling reactions are used to convert the now readily available 3,4-dibromopyrrole derivatives 13 and 26 into the core structures of different pyrrole alkaloids. Several compounds of this series exhibit respe
Total syntheses of ningalin A, lamellarin O, lukianol A, and permethyl storniamide A utilizing heterocyclic azadiene Diels - Alder reactions
Boger, Dale L.,Boyce, Christopher W.,Labroli, Marc A.,Sehon, Clark A.,Jin, Qing
, p. 54 - 62 (2007/10/03)
Concise, efficient total syntheses of ningalin A (1), lamellarin O (2), lukianol A (3), and permethyl storniamide A (5) are detailed on the basis of a common heterocyclic azadiene Diels-Alder strategy (1,2,4,5-tetrazine → 1,2-diazine → pyrrole) ideally suited for construction of the densely functionalized pyrrole cores found in the three classes of marine natural products. Examination of the natural products and a number of synthetic intermediates revealed that some including lamellarin O (2) and lukianol A (3) exhibit modest cytotoxic activity against both wild-type and multidrug- resistant tumor cell lines. Fundamentally more important, a new class of agents including permethyl storniamide A (5) and its precursor 30, which lack inherent cytotoxic activity, are disclosed which reverse the multidrug- resistant (MDR) phenotype, resensitizing a human colon cancer cell line (HCT116/VM46) to vinblastine and doxorubicin at lower doses than the prototypical agent verapamil.
