64188-97-2Relevant articles and documents
Synthesis of 2-aryl quinazolinones: Via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds
Jang, Yoonkyung,Lee, Seok Beom,Hong, Junhwa,Chun, Simin,Lee, Jeeyeon,Hong, Suckchang
supporting information, p. 5435 - 5441 (2020/08/03)
Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95percent. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles. This journal is
Substrate Profiling of the Cobalt Nitrile Hydratase from Rhodococcus rhodochrous ATCC BAA 870
Mashweu, Adelaide R.,Chhiba‐Govindjee, Varsha P.,Bode, Moira L.,Brady, Dean
, (2020/01/13)
The aromatic substrate profile of the cobalt nitrile hydratase from Rhodococcus rhodochrous ATCC BAA 870 was evaluated against a wide range of nitrile containing compounds (>60). To determine the substrate limits of this enzyme, compounds ranging in size from small (90 Da) to large (325 Da) were evaluated. Larger compounds included those with a biaryl axis, prepared by the Suzuki coupling reaction, Morita–Baylis–Hillman adducts, heteroatomlinked diarylpyridines prepared by Buchwald–Hartwig crosscoupling reactions and imidazo[1,2a]pyridines prepared by the Groebke–Blackburn–Bienaymé multicomponent reaction. The enzyme active site was moderately accommodating, accepting almost all of the small aromatic nitriles, the diarylpyridines and most of the biaryl compounds and Morita–Baylis–Hillman products but not the Groebke–Blackburn–Bienaymé products. Nitrile conversion was influenced by steric hindrance around the cyano group, the presence of electron donating groups (e.g., methoxy) on the aromatic ring, and the overall size of the compound.
Design, synthesis and biological activities of 2,3-dihydroquinazolin-4(1H)-one derivatives as TRPM2 inhibitors
Zhang, Han,Liu, Huan,Luo, Xiao,Wang, Yuxi,Liu, Yuan,Jin, Hongwei,Liu, Zhenming,Yang, Wei,Yu, Peilin,Zhang, Liangren,Zhang, Lihe
, p. 235 - 252 (2018/05/09)
Transient receptor potential melastatin 2 (TRPM2), a Ca2+-permeable cationic channel, plays critical roles in insulin release, cytokine production, body temperature regulation and cell death as a reactive oxygen species (ROS) and temperature sensor. However, few TRPM2 inhibitors have been reported, especially TRP-subtype selective inhibitors, which hampers the investigation and validation of TRPM2 as a drug target. To discover novel TRPM2 inhibitors, 3D similarity-based virtual screening method was employed, by which 2,3-dihydroquinazolin-4(1H)-one derivative H1 was identified as a TRPM2 inhibitor. A series of novel 2,3-dihydroquinazolin-4(1H)-one derivatives were subsequently synthesized and characterized. Their inhibitory activities against the TRPM2 channel were evaluated by calcium imaging and electrophysiology approaches. Some of the compounds exhibited significant inhibitory activity, especially D9 which showed an IC50 of 3.7 μM against TRPM2 and did not affect the TRPM8 channel. The summarized structure-activity relationship (SAR) provides valuable insights for further development of specific TRPM2 targeted inhibitors.
Synthesis of Novel Hydroxymethyl-Substituted Fused Heterocycles
Holmes, Jane L.,Almeida, Lynsie,Barlaam, Bernard,Croft, Rosemary A.,Dishington, Allan P.,Gingipalli, Laksmaiah,Hassall, Lorraine A.,Hawkins, Janet L.,Ioannidis, Stephanos,Johannes, Jeffrey W.,McGuire, Thomas M.,Moore, Jane E.,Patel, Anil,Pike, Kurt G.,Pontz, Timothy,Wu, Xiaoyun,Wang, Tao,Zhang, Hai-Jun,Zheng, Xiaolan
supporting information, p. 1226 - 1234 (2016/05/19)
Examples of hydroxymethylated analogues of heteroaryl cores such as quinazolin-4-ones, isoquinolin-1(2H)-ones, pyrido[3,4-d]pyrimidin-4(3H)-ones, chromen-4-ones and pyrrolo[2,1-f][1,2,4]triazin-4(3H)-ones are sparse or non-existent in the scientific literature. We have demonstrated that such compounds are accessible by using standard procedures from readily available raw materials.
HETEROCYCLIC COMPOUNDS AND USES THEREOF
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Paragraph 00674-00676, (2013/03/26)
Compounds and pharmaceutical compositions that modulate kinase activity, including PI3 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including PI3 kinase activity, are described herein.
2-Aminomethylphenylamine as a novel scaffold for factor Xa inhibitor
Mochizuki, Akiyoshi,Nagata, Tsutomu,Kanno, Hideyuki,Suzuki, Makoto,Ohta, Toshiharu
experimental part, p. 1623 - 1642 (2011/04/21)
We have been researching orally active factor Xa inhibitor for a long time. We explored the new diamine linker using effective ligands to obtain a new attractive original scaffold 2-aminomethylphenylamine derivative. Compound 1D showed very strong in vitro and in vivo factor Xa inhibitory activity, as well as favorable PK profiles in po administration to monkeys.
SUBSTITUTED RING FUSED AZINES AND THEIR USE IN CANCER THERAPY
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Page/Page column 24-25, (2010/11/28)
The present invention relates to substituted ring fused azines and methods of using said compounds in treating cancers. More specifically, the present invention relates to the preparation of 4-alkyl-2-(heterocyclic)-azines and their use as cancer agents o
Preparation of 4-substituted 3-amino-2-chloropyridines, synthesis of a nevirapine analogue
Bakke,Riha
, p. 99 - 104 (2007/10/03)
A new method for preparing 3-amino-2-chloropyridines with a substituent (methyl, phenyl, carboxamide, methoxycarbonyl, acetyl, benzoyl and cyano) at the 4-position has been developed. An isoquinoline analogue of the reverse transcriptase inhibitor Nevirapine has been synthesized from the 4-amino-3-chloroisoquinoline.