62300-07-6Relevant articles and documents
Identification of BR102910 as a selective fibroblast activation protein (FAP) inhibitor
Jung, Hui Jin,Nam, Eun Hye,Park, Jin Young,Ghosh, Prithwish,Kim, In Su
supporting information, (2021/02/26)
Fibroblast activation protein (FAP) belongs to the family of prolyl-specific serine proteases and displays both exopeptidase and endopeptidase activities. FAP expression is undetectable in most normal adult tissues, but is greatly upregulated in sites of tissue remodeling, which include fibrosis, inflammation and cancer. Due to its restricted expression pattern and dual enzymatic activities, FAP inhibition is investigated as a therapeutic option for several diseases. In the present study, we described the structure–activity relationship of several synthesized compounds against DPPIV and prolyl oligopeptidase (PREP). In particular, BR102910 (compound 24) showed nanomolar potency and high selectivity. Moreover, the in vivo FAP inhibition study of BR102910 (compound 24) using C57BL/6J mice demonstrated exceptional profiles and satisfactory FAP inhibition efficacy. Based on excellent in vitro and in vivo profiles, the potential of BR102910 (compound 24) as a lead candidate for the treatment of type 2 diabetes is considered.
N-Alkenylation of hydroxamic acid derivatives with ethynyl benziodoxolone to synthesizecis-enamides through vinyl benziodoxolones
Shimbo, Daisuke,Maruyama, Toshifumi,Tada, Norihiro,Itoh, Akichika
supporting information, p. 2442 - 2447 (2021/04/02)
The stereoselective synthesis ofcis-β-N-alkoxyamidevinyl benziodoxolones (cis-β-N-RO-amide-VBXs) fromO-alkyl hydroxamic acids in the presence of an ethynyl benziodoxolone-acetonitrile complex (EBX-MeCN) is reported herein. The reaction was performed under mild conditions including an aqueous solvent, a mild base, and room temperature. The reaction tolerated variousO-alkyl hydroxamic acids derived from carboxylic acids, such as amino acids, pharmaceuticals, and natural products. Vinyl dideuteratedcis-β-N-MeO-amide-VBXs were also synthesized using deuterium oxide as the deuterium source. Valine-derivedcis-β-N-MeO-amide-VBX was stereospecifically derivatized to hydroxamic acid-derivedcis-enamides without the loss of stereoselectivity or reduction in the deuterium/hydrogen ratio.
FUSED [1,2,4]THIADIAZINE DERIVATIVES WHICH ACT AS KAT INHIBITORS OF THE MYST FAMILY
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Page/Page column 84; 85, (2019/03/17)
A compound of formula (I): which inhibits the activity of one or more KATs of the MYST family, i.e., TIP60, KAT6B, MOZ, HBO1 and MOF.
Rhodium(III)-Catalyzed Cascade Cyclization/Electrophilic Amidation for the Synthesis of 3-Amidoindoles and 3-Amidofurans
Hu, Zhiyong,Tong, Xiaofeng,Liu, Guixia
supporting information, p. 2058 - 2061 (2016/06/01)
A rhodium(III)-catalyzed cascade cyclization/electrophilic amidation using N-pivaloyloxylamides as the electrophilic nitrogen source has been developed. This protocol provides an efficient route for the synthesis of 3-amidoindoles and 3-amidofurans under mild conditions with good functional group tolerance. The synthetic utility of this reaction has been demonstrated through the derivatization of the 3-amidoindoles to several heterocycle-fused indoles.
6π/10π-Electrocyclization of ketene-iminium salts for the synthesis of substituted naphthylamines
Villedieu-Percheron, Emmanuelle,Catak, Saron,Zurwerra, Didier,Staiger, Roman,Lachia, Mathilde,De Mesmaeker, Alain
, p. 2446 - 2449 (2014/05/06)
An intramolecular 6π/10π-electrocyclization from ketene-iminium salts was developed for the preparation of naphthylamines. Various substituents on the nitrogen, on the aromatic ring, and on the olefin were studied. Tricyclic skeletons were obtained in few steps and good overall yields. The electrocyclization of ketene-iminium salts has been computationally explored by means of DFT calculations and their activation barriers were compared to the parent triene as well as the corresponding dienyl allenes and dienyl ketenes. Electrocyclizations for ketene-iminium salts were shown to be highly exergonic and have much smaller barriers to activation.
Synthesis of strigolactones analogues by intramolecular [2+2] cycloaddition of ketene-iminium salts to olefins and their activity on Orobanche cumana seeds
Lachia, Mathilde,Wolf, Hanno Christian,De Mesmaeker, Alain
, p. 2123 - 2128 (2014/05/06)
Strigolactones have been the latest identified phytohormones. Among the strigolactones analogues described recently, GR-24 remains the most studied derivative which is used as standard in this field. In order to improve several properties of GR-24 for pot
Chiral aryl iodide-catalyzed enantioselective α-oxidation of ketones
Rodriguez, Arantxa,Moran, Wesley J.
experimental part, p. 1178 - 1182 (2012/06/01)
Several chiral aryl iodides were synthesized and assessed as catalysts in the enantioselective α-oxytosylation of propiophenone and the oxidative cyclization of 5-oxo-5-phenylpentanoic acid to 5-benzoyldihydrofuran-2(3H)-one. The highest enantioselectivit
STRIGOLACTAM DERIVATIVES AND THEIR USE AS PLANT GROWTH REGULATORS
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Page/Page column 30-31, (2012/06/30)
The present invention relates to novel strigolactam derivatives of formula (I) to processes and intermediates for preparing them, to plant growth regulator compositions comprising them and to methods of using them for controlling the growth of plants and/
A novel approach toward the synthesis of strigolactones through intramolecular [2+2] cycloaddition of ketenes and ketene-iminiums to olefins. Application to the asymmetric synthesis of GR-24
Lachia, Mathilde,Jung, Pierre M.J.,De Mesmaeker, Alain
scheme or table, p. 4514 - 4517 (2012/10/07)
An intramolecular [2+2] cycloaddition of ketenes and ketene-iminium was developed for the preparation of GR-24, a synthetic analogue of the family of strigolactone plant hormones. Excellent levels of regioselectivity and of chiral induction were obtained
Facile synthesis of coumarin- and quinolone-annulated benzazoninone derivatives by an intramolecular heck reaction strategy via 9- exo -trig cyclization
Majumdar,Ghosh, Tapas,Samanta, Srikanta
experimental part, p. 1569 - 1574 (2011/06/24)
A synthetic strategy based on the application of the aromatic aza-Claisen rearrangement followed by an intramolecular Heck reaction sequence as the key step has been developed for the regiocontrolled synthesis of hitherto unreported coumarin- and quinolon
