6326-79-0Relevant articles and documents
Saccharomonosporine A inspiration; synthesis of potent analogues as potential PIM kinase inhibitors
Abdel-Rahman, Hamdy M.,Abdelmohsen, Usama Ramadan,Aboulmagd, Asmaa M.,Hassan, Hossam M.,Sayed, Ahmed M.
, p. 6752 - 6762 (2020/03/03)
Saccharomonosporine A was recently reported as a natural anti-cancer agent working through inhibition of a Proviral integration site for Moloney murine leukemia virus-1 (PIM-1) kinase. Structural bioisosteres of this natural product were synthesized and t
NaI-mediated divergent synthesis of isatins and isoindigoes: A new protocol enabled by an oxidation relay strategy
Zhang, Hong-Hua,Wang, Yong-Qiang,Huang, Long-Tao,Zhu, Long-Qing,Feng, Yi-Yue,Lu, Ying-Mei,Zhao, Quan-Yi,Wang, Xue-Qiang,Wang, Zhen
supporting information, p. 8265 - 8268 (2018/07/29)
A new approach for the synthesis of isatins and isoindigoes by an inexpensive and environmentally friendly NaI-mediated transformation is disclosed. The selectivity could be switched by simply varying the solvent, and isatins (using THF) and isoindigoes (using DMSO) could be obtained in moderate to excellent yields.
Methylisoindigo and its bromo-derivatives are selective tyrosine kinase inhibitors, repressing cellular stat3 activity, and target CD133+ cancer stem cells in PDAC
Tegethoff, Jana,Bischoff, Roland,Saleh, Sawsan,Blagojevic, Biljana,Merz, Karl-Heinz,Cheng, Xinlai
, (2017/09/25)
Indirubin is an active component of the herbal ingredient 'Danggui Longhui wan', which was used for the treatment of inflammation and chronic myeloid leukemia in China. The recent study showed its derivative methylisoindigo (also known as meisoindigo) preferentially targeting cancer stem cells (CSCs) in interference with AMPK and LKB1, the cellular metabolic sensors. In this study, we screened the effect of meisoindigo on a panel of 300 protein kinases and found that it selectively inhibited Stat3-associated tyrosine kinases and further confirmed its activity in cell based assays. To gain a deeper insight into the structure-activity relationship we produced 7 bromo-derivatives exhausting the accessible positions on the bisindole backbone except for in the 4-position due to the space limitation. We compared their anti-proliferative effects on tumor cells. We found that 6-bromomeisoindigo showed improved toxicity in company with increased Stat3 inhibition. Moreover, we detected that 6-bromomeisoindigo induced apoptosis of 95% of CD133+ pancreatic cancer cells. Considering that CD133 is a common marker highly expressed in a range of CSCs, our results imply the potential application of 6-bromomeisoindigo for the treatment of CSCs in different types of cancers.
Utilizing Solubility differences to achieve regiocontrol in the synthesis of substituted quinoline-4-carboxylic acids
Lindsay-Scott, Peter J.,Barlow, Helen
supporting information, p. 1516 - 1520 (2016/06/14)
A practical method for the regiocontrolled synthesis of substituted quinoline-4-carboxylic acids is described. Solubility differences between the product quinoline regioisomers enable their facile separation, thus avoiding any challenging chromatographic purifications and allowing access to highly substituted quinoline compounds in three steps from commercially available anilines.
Novel synthesis of 4-or 6-substituted indirubin derivatives
Zhang, Aiying,Yu, Mingfeng,Lan, Tian,Liu, Zenglu,Mao, Zhenmin
experimental part, p. 3125 - 3134 (2010/12/24)
A simple and convenient route for synthesis of a series of 4-or 6-substituted indirubin derivatives by oxidation and subsequent condensation of indoxyl and isatin is described. Acidic reaction conditions are crucial to the condensation of 4-substituted derivatives, whereas for the condensation of 6-substituted derivatives, both acidic and basic conditions work well. Copyright Taylor & Francis Group, LLC.
Structure - activity relationship studies leading to the identification of (2E)-3-[l-[(2,4-dichlorophenyl)methyl]-5-fluoro-3-methyl-lH-indol-7-yl]-N-[(4, 5-dichloro-2-thienyl)sulfonyl]-2-propenamide (DG-041), a potent and selective prostanoid EP3 receptor antagonist, as a novel antiplatelet agent that does not prolong bleeding
Singh, Jasbir,Zeller, Wayne,Zhou, Nian,Hategan, Georgeta,Mishra, Rama K.,Polozov, Alex,Yu, Peng,Onua, Emmanuel,Zhang, Jun,Ramírez, José L.,Sigthorsson, Gudmundur,Thorsteinnsdottir, Margret,Kiselyov, Alex S.,Zembower, David E.,Andrésson, Thorkell,Gurney, Mark E.
supporting information; experimental part, p. 18 - 36 (2010/04/26)
The EP3 receptor on the platelet mediates prostaglandin E 2 potentiation of thrombogenic coagonists including collagen and adenosine diphosphate (ADP). A pharmacophore driven approach led to the identification of diverse peri-substituted heterocycles as potent and selective EP3 receptor antagonists. A simultaneous chemical optimization and druglike assessment of prioritized molecules converged on a lead compound 50 (DG-041) that displayed favorable in vitro and functional activities as an inhibitor of human platelet aggregation. This agent is currently in human clinical trials for the treatment of atherothrombosis.
Counter-current chromatography separation of isatin derivatives using the sandmeyer methodology
Almeida, Ma?rcia R.,Leita?o, Gilda G.,Silva, Ba?rbara V.,Barbosa, Jussara P.,Pintoa, Angelo C.
scheme or table, p. 764 - 769 (2010/08/13)
A rapid and efficient method, using high-speed counter-current chromatography (HSCCC) technique, was developed for the separation of isomeric isatin derivatives, prepared following the Sandmeyer route. The biphasic solvent system composed of hexane:ethyl acetate:ethanol:water 1:0.5:0.5:1 (v/v/v/v) was used for all separations.
Bacterial translation inhibitors, 1-acylindazol-3-ols as anthranilic acid mimics
Stiff, Cory,Graber, David R.,Thorarensen, Atli,Wakefield, Brian D.,Marotti, Keith R.,Melchior, Earline P.,Sweeney, Michael T.,Han, Fusen,Rohrer, Douglas C.,Zurenko, Gary E.,Romero, Donna L.
scheme or table, p. 6293 - 6297 (2009/07/18)
The discovery and initial optimization of a novel anthranilic acid derived class of antibacterial agents has been described in a recent series of papers. This paper describes the discovery of 1-acylindazol-3-ols as a novel bioisostere of an anthranilic acid. The synthesis and structure-activity relationships of the indazol bioisosteres are described herein.
CARBOXYLIC ACID PERI - SUBSTITUTED BICYCLICS FOR OCCLUSIVE ARTERY DISEASE
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Page/Page column 118, (2010/11/08)
Peri-substituted, fused bicyclic ring carboxylic acids useful for the treatment or prophylaxis of a prostaglandin-mediated disease or condition are disclosed.
INDIRUBIN-TYPE COMPOUNDS, COMPOSITIONS, AND METHODS FOR THEIR USE
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Page/Page column 24; Figure 2A, (2008/06/13)
Compounds and compositions including 6-bromo-indirubin, 5-amino-indirubin and N-methyl-indirubins and related indirubin derivatives are provided that are useful as selective modulators of glycogen synthase kinase-3, cyclin-dependent protein kinases or aryl hydrocarbon receptors. Methods of inhibiting or modulating cell growth or cell cycling are provided using the compounds of the invention. In other aspects, compounds and methods for the treatment of protozoan-mediated diseases, Alzheimer's disease and diabetes are provided.