567-61-3Relevant articles and documents
Insights into 6-Methylsalicylic Acid Bio-assembly by Using Chemical Probes
Parascandolo, James S.,Havemann, Judith,Potter, Helen K.,Huang, Fanglu,Riva, Elena,Connolly, Jack,Wilkening, Ina,Song, Lijiang,Leadlay, Peter F.,Tosin, Manuela
, p. 3463 - 3467 (2016)
Chemical probes capable of reacting with KS (ketosynthase)-bound biosynthetic intermediates were utilized for the investigation of the model type I iterative polyketide synthase 6-methylsalicylic acid synthase (6-MSAS) in vivo and in vitro. From the fermentation of fungal and bacterial 6-MSAS hosts in the presence of chain termination probes, a full range of biosynthetic intermediates was isolated and characterized for the first time. Meanwhile, in vitro studies of recombinant 6-MSA synthases with both nonhydrolyzable and hydrolyzable substrate mimics have provided additional insights into substrate recognition, providing the basis for further exploration of the enzyme catalytic activities. Chemical probes capable of reacting with KS (ketosynthase)-bound biosynthetic intermediates were utilized for the investigation of the model type I iterative polyketide synthase 6-methylsalicylic acid synthase (6-MSAS) in vivo and in vitro. From the fermentation of fungal and bacterial 6-MSAS hosts in the presence of chain termination probes, a full range of biosynthetic intermediates was isolated (see examples) and characterized.
Palladium-catalyzed ortho-C-H hydroxylation of benzoic acids
Luo, Feihua,He, Shuhua,Gou, Quan,Chen, Jinyang,Zhang, mingzhong
, (2021/10/06)
A simple Pd(OAc)2 catalyzed ortho-hydroxylation of benzoic acids using TBHP as the sole oxidant has been explored. This protocol features relatively broad substrate scope and operational simplicity. The compatibility of ortho-substituted substrates is an effective complement to the previous ortho-hydroxylation reaction.
Copper-Catalyzed One-Pot Synthesis of Dibenzofurans, Xanthenes, and Xanthones from Cyclic Diphenyl Iodoniums
Zhu, Daqian,Li, Min,Wu, Zhouming,Du, Yongliang,Luo, Bingling,Huang, Peng,Wen, Shijun
supporting information, p. 4566 - 4571 (2019/07/09)
Oxygenation of cyclic diphenyl iodoniums (CDPIs) with varied medium-ring sizes has been fully investigated. This practical copper-catalyzed tandem reaction of CDPIs with water as the oxygen source enables the construction of derivatised dibenzofurans and xanthenes at moderate to good yields. Moreover, structurally important xanthones are also successfully accessed under the oxygenation conditions with additional TEMPO.
Direct ortho-Acyloxylation of Arenes and Alkenes by Cobalt Catalysis
Lin, Cong,Chen, Zhengkai,Liu, Zhanxiang,Zhang, Yuhong
, p. 519 - 532 (2018/02/09)
An efficient protocol for the cobalt-catalyzed acyloxylation of arenes and alkenes with the assistance of an 8-aminoquinolyl auxiliary group is reported. In this transformation, benzoic acids, alkenyl acids, and aliphatic acids could be readily involved to afford structurally diverse esters. It is worth noting that the silver sulfate (Ag2SO4) oxidant is renewable and the directing group could be removed and recycled. The strategy represents the first successful example of transition metal-catalyzed acyloxylation of alkenyl carboxamides C(sp2)?H bonds with carboxylic acids. (Figure presented.).
Valuable building block for the synthesis of lunularic acid, hydrangeic acid and their analogues
Mukkamala, Ramesh,Hossain, Asik,Singh Aidhen, Indrapal
, p. 1085 - 1090 (2017/01/28)
A new functionalised sulphone-based building block has been synthesised that enabled C-C bond formation through Julia olefination. The utility of developed building block was demonstrated by successful synthesis of two natural products lunularic acid, hydrangeic acid and initial libraries of their analogues.
Carboxylation of Phenols with CO2 at Atmospheric Pressure
Luo, Junfei,Preciado, Sara,Xie, Pan,Larrosa, Igor
supporting information, p. 6798 - 6802 (2016/05/11)
A convenient and efficient method for the ortho-carboxylation of phenols under atmospheric CO2 pressure has been developed. This method provides an alternative to the previously reported Kolbe-Schmitt method, which requires very high pressures of CO2. The addition of a trisubstituted phenol has proved essential for the successful carboxylation of phenols with CO2 at standard atmospheric pressure, allowing the efficient preparation of a broad variety of salicylic acids.
Metabolically stable dibenzo[ b, e ]oxepin-11(6 H)-ones as highly selective p38 MAP kinase inhibitors: Optimizing anti-cytokine activity in human whole blood
Baur, Benjamin,Storch, Kirsten,Martz, Kathrin E.,Goettert, Marcia I.,Richters, André,Rauh, Daniel,Laufer, Stefan A.
supporting information, p. 8561 - 8578 (2013/12/04)
Five series of metabolically stable disubstituted dibenzo[b,e]oxepin-11(6H) -ones were synthesized and tested in a p38α enzyme assay for their inhibition of tumor necrosis factor-α (TNF-α) release in human whole blood. Compared to the monosubstituted dibenzo[b,e]oxepin-11(6H)-one derivatives, it has been shown that the additional introduction of hydrophilic residues at position 9 leads to a substantial improvement of the inhibitory potency and metabolic stability. Using protein X-ray crystallography, the binding mode of the disubstituted dibenzoxepinones and the induction of a glyince flip in the hinge region were confirmed. The most potent compound of this series, 32e, shows an outstanding biological activity on isolated p38α, with an IC50 value of 1.6 nM, extraordinary selectivity (by a factor >1000, Kinase WholePanelProfiler), and low ATP competitiveness. The ability to inhibit the release of TNF-α from human whole blood was optimized down to an IC50 value of 125 nM. With the promising dibenzoxepinone inhibitor 3i, a pharmacokinetic study in mice was conducted.
COMPOUNDS WITH 7-MEMBER CYCLE AND THE PHARMACEUTICAL USE THEREOF FOR PREVENTING AND TREATING DIABETES AND METABOLISM SYNDROME
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Page/Page column 33, (2010/07/06)
The invention discloses a new use of a class of heptacyclic compounds in the preparation of formulations for the prevention and treatment of diabetes and metabolic syndromes; the present invention also discloses a new class of heptacyclic compounds; the present invention also discloses a process for preparing the heptacyclic compounds and a composition containing the same. The heptacyclic compounds of the present invention can be used to effectively preventing or treating diseases such as diabetes and metabolic syndromes.
CARBAZOLE CARBOXAMIDE COMPOUNDS USEFUL AS KINASE INHIBITORS
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Page/Page column 33-34, (2010/07/04)
Compounds having the formula (I), and enantiomers, and diastereomers, pharmaceutically-acceptable salts, thereof, are useful as kinase modulators, including Btk modulation.
Enediyne antitumor antibiotic maduropeptin biosynthesis featuring a C-methyltransferase that acts on a COA-Tethered aromatic substrate
Ling, Jianya,Horsman, Geoffrey P.,Huang, Sheng-Xiong,Luo, Yinggang,Lin, Shuangjun,Shen, Ben
supporting information; experimental part, p. 12534 - 12536 (2010/11/04)
The enediyne antitumor antibiotic maduropeptin (MDP) is produced by Actinomadura madurae ATCC 39144. The biosynthetic pathway for the 3,6-dimethylsalicylic acid moiety of the MDP chromophore is proposed to be comprised of four enzymes: MdpB, MdpB1, MdpB2, and MdpB3. Based on the previously characterized biosynthesis of the naphthoic acid moiety of neocarzinostatin (NCS), we expected a biosynthetic pathway featuring carboxylic acid activation by the MdpB2 CoA ligase immediately before its coupling to an enediyne core intermediate. Surprisingly, the MDP aromatic acid biosynthetic pathway employs an unusual logic in which MdpB2-catalyzed CoA activation occurs before MdpB1-catalyzed C-methylation, demonstrating that MdpB1 is apparently unique in its ability to C-methylate a CoA-tethered aromatic acid. MdpB2 is a promiscuous CoA ligase capable of activating a variety of salicylic acid analogues, a property that could be potentially exploited to engineer MDP analogues.
