42174-79-8Relevant academic research and scientific papers
Asymmetric total synthesis of dihydroisocoumarins: 6-methoxymellein, kigelin and fusarentin 6, 7 dimethyl ether by employing proline catalysed asymmetric α-aminoxylation
Mane, Baliram B.,Markad, Sachin B.,Waghmode, Suresh B.
, (2020/10/19)
A concise asymmetric total synthesis of dihydroisocoumarins such as 6-methoxymellein, kigelin and fusarentin 6,7-dimethyl ether in high enantiopurity have been achieved from non-chiral aldehydes by employing proline catalysed asymmetric α-aminoxylation reaction. The required stereochemistry of hydroxyl group have been generated by alternating L or D proline as a organocatalyst in α-aminoxylation step and lactone ring is assembled by oxa-Pictet-Spengler cyclisation reaction as the key steps.
Piperlongumine derived cyclic sulfonamides (sultams): Synthesis and in?vitro exploration for therapeutic potential against HeLa cancer cell lines
Lad, Nitin P.,Kulkarni, Sarang,Sharma, Rajiv,Mascarenhas, Malcolm,Kulkarni, Mahesh R.,Pandit, Shivaji S.
, p. 870 - 878 (2016/12/18)
A novel modification of piperlongumine is designed, bearing a cyclic sulphonamide (sultam) and its synthesis is described. For the first time herein we report the synthesis and biological evaluation of the natural product derived cyclic sulfonamides using Grubbs second generation catalyst (Grubbs II) via ring closing metathesis approach. Synthesis of a series of piperlongumine derived sultams is done in a moderate to good yield using Wittig reaction, Ring-Closing Metathesis (RCM) and, amide synthesis by using mixed anhydride, approach. All synthesized compounds were evaluated for anticancer activity and some demonstrated dose dependent reduction in HeLa cell growth. Of these 7, 10 and 14 significantly reduced the cell growth. Consequently their calculated GI50values were found to be 0.1 or 0.1?μM.
Design, synthesis, and evaluation of 2-piperidone derivatives for the inhibition of β-amyloid aggregation and inflammation mediated neurotoxicity
Li, Lei,Chen, Ming,Jiang, Feng-Chao
, p. 1853 - 1865 (2016/04/05)
A series of novel multipotent 2-piperidone derivatives were designed, synthesized and biologically evaluated as chemical agents for the treatment of Alzheimer's disease (AD). The results showed that most of the target compounds displayed significant potency to inhibit Aβ1-42 self-aggregation. Among them, compound 7q exhibited the best inhibition of Aβ1-42 self-aggregation (59.11% at 20 μM) in a concentration-dependent manner. Additionally, the compounds 6b, 7p and 7q as representatives were found to present anti-inflammation properties in lipopolysaccharide (LPS)-induced microglial BV-2 cells. They could effectively suppress the production of pro-inflammatory cytokines such as TNF-α, IL-1β and IL-6. Meanwhile, compound 7q could prevent the neuronal cell SH-SY5Y death by LPS-stimulated microglia cell activation mediated neurotoxicity. The molecular modeling studies demonstrated that compounds matched the pharmacophore well and had good predicted physicochemical properties and estimated IC50 values. Moreover, compound 7q exerted a good binding to the active site of myeloid differentiation factor 88 (MyD88) through the docking analysis and could interfere with its homodimerization or heterodimerization. Consequently, these compounds emerged as promising candidates for further development of novel multifunctional agents for AD treatment.
Design, synthesis and biological evaluation of pyrazolylaminoquinazoline derivatives as highly potent pan-fibroblast growth factor receptor inhibitors
Fan, Jun,Dai, Yang,Shao, Jingwei,Peng, Xia,Wang, Chen,Cao, Sufen,Zhao, Bin,Ai, Jing,Geng, Meiyu,Duan, Wenhu
supporting information, p. 2594 - 2599 (2016/05/09)
Fibroblast growth factor receptors (FGFRs) are important oncology targets due to the dysregulation of this signaling pathway in a wide variety of human cancers. We identified a series of pyrazolylaminoquinazoline derivatives as potent FGFR inhibitors with low nanomolar potency. The representative compound 29 strongly inhibited FGFR1-3 kinase activity and suppressed FGFR signaling transduction in FGFR-addicted cancer cells; FGFRs-driven cell proliferation was also strongly inhibited regardless of mechanistic complexity implicated in FGFR activation, which further confirmed that 29 was a potent pan-FGFR inhibitor. The flexibility of our structure offered the potential to preserve good affinity for mutant FGFR, which is important for developing TKIs with long-term efficacy.
Design and synthesis of a series of serine derivatives as small molecule inhibitors of the SARS coronavirus 3CL protease
Konno, Hiroyuki,Wakabayashi, Masaki,Takanuma, Daiki,Saito, Yota,Akaji, Kenichi
, p. 1241 - 1254 (2016/03/01)
Synthesis of serine derivatives having the essential functional groups for the inhibitor of SARS 3CL protease and evaluation of their inhibitory activities using SARS 3CL R188I mutant protease are described. The lead compounds, functionalized serine derivatives, were designed based on the tetrapeptide aldehyde and Bai's cinnamoly inhibitor, and additionally performed with simulation on GOLD softwear. Structure activity relationship studies of the candidate compounds were given reasonable inhibitors ent-3 and ent-7k against SARS 3CL R188I mutant protease. These inhibitors showed protease selectivity and no cytotoxicity.
NRF2 REGULATORS
-
Page/Page column 214; 215, (2015/07/07)
The present invention relates to bis aryl analogs, pharmaceutical compositions containing them and their use as Nrf2 regulators.
Synthesis of 2,3-syn-diarylpent-4-enamides via acyl-Claisen rearrangements of substituted cinnamyl morpholines: Application to the synthesis of magnosalicin
Dickson, Benjamin D.,Dittrich, Nora,Barker, David
scheme or table, p. 4464 - 4468 (2012/09/25)
The acyl-Claisen rearrangement of substituted phenylacetyl chlorides and cinnamyl morpholines gives 2,3-syn-diarylpent-4-enamides. Electron-rich cinnamyl morpholines containing alkoxy substituents only reacted with phenylacetyl chlorides; replacement of t
Synthesis of some phenylpropanoid glycosides (PPGs) and their acetylcholinesterase/xanthine oxidase inhibitory activities
Li, Xiao-Dong,Kang, Shuai-Tao,Li, Guo-Yu,Li, Xian,Wang, Jin-Hui
experimental part, p. 3580 - 3596 (2011/07/07)
In this research, three categories of phenylpropanoid glycosides (PPGs) were designed and synthesized with PPGs isolated from Rhodiola rosea L. as lead compounds. Their inhibitory abilities toward acetylcholinesterase (AChE) and xanthine oxidase (XOD) were also tested. Some of the synthetic PPGs exhibited excellent enzyme inhibitory abilities.
Practical one-pot syntheses of ethyl 4-substituted-1 H-pyrrole-3- carboxylates from aldehydes
Chang, Jay Hyok,Shin, Hyunik
, p. 291 - 293 (2013/01/03)
Ethyl 4-substituted-1H-pyrrole-3-carboxylates were prepared in a one-pot manner starting from aromatic or aliphatic aldehydes via a Horner-Wadsworth- Emmons reaction and subsequent reaction with tosylmethylisocyanide (TosMIC) in the presence of sodium tert-amylate in toluene. Judicious selection of base and solvent led to the use of a single solvent, i.e., toluene, for reactions as well as for crystallization to render the one-pot process more practical and greener than the stepwise version. hisin@ lels.com.
A microwave-accelerated esterification of α,β-unsaturated acids with alkyl or aryl carbonochloridate and triethylamine in acetonitrile as a novel esterifying reagent mixture
Pathania, Vinod,Sharma, Anuj,Sinha, Arun K.
, p. 811 - 816 (2007/10/03)
An efficient synthesis of α,β-unsaturated esters by treatment of the corresponding acids with alkyl or aryl carbonochloridate, triethylamine, and acetonitrile was accomplished for the first time under microwave irradiation for 10 min. The esters 1b-24b were isolated in 71-97% yield.
