28752-82-1Relevant academic research and scientific papers
Pericyclic reactions of azafulvenium methides bearing internal dipolarophiles - synthesis of chromene and chromane derivatives
Ribeiro Laia, Fernanda M.,Soares, Maria I. L.,Gomes, Clara S. B.,Pinho E Melo, Teresa M. V. D.
, p. 1341 - 1354 (2015)
The reactivity of azafulvenium methides with internal dipolarophiles was explored as an approach to new chromene derivatives. 4,5-Dimethoxycarbonyl- and 5-ethoxycarbonyl- 4-phenylazafulvenium methides with a prop-2-ynyloxyphenyl substituent are converted into 2-[2-(2H-chromen- 8-yl)vinyl]-1H-pyrroles through a sequence of rearrangements. 4,5-Dimethoxycarbonylazafulvenium methide with a more-activated dipolarophile as well as the more-activated 5- (trifluoromethyl)azafulvenium methide with an unactivated alkyne could be trapped by [8π+2π] cycloadditions to afford 8,12a-dihydro-6H-chromeno[4,3-e]indolizines. 5-(Trifluoromethyl) azafulvenium methide with a 2-(3-methoxycarbonylprop- 2-enyloxy)phenyl substituent at C-1 participated in both intramolecular [8π+2π] and [4π+2π] cycloadditions to afford heterocycle-fused chromanes. The microwave-induced rearrangements of 3-[2-(prop-2-ynyloxy)phenyl]-1H,3Hpyrrolo[ 1,2-c]thiazoles afforded chiral 3-(2H-chromen-8-yl)- 1H,3H-pyrrolo[1,2-c]thiazoles.
An expedient strategy for the diversity-oriented synthesis of macrocyclic compounds with natural product-like characteristics
Ciardiello, Joe J.,Galloway, Warren R.J.D.,O'Connor, Cornelius J.,Sore, Hannah F.,Stokes, Jamie E.,Wu, Yuteng,Spring, David R.
, p. 3567 - 3578 (2016)
Naturally-derived macrocyclic compounds are associated with a diverse range of biological activities, including antibacterial effects, and there are over 100 marketed macrocycle drugs derived from natural products. However, synthetic macrocycles are widely considered to be poorly explored in antibiotic development (indeed, within drug discovery in general). This has been attributed to challenges associated with the generation of such compounds. Whilst there are synthetic methods that can produce large collections of structurally similar macrocycles (i.e., compounds with varying appendages based around similar core macrocyclic ring architectures) there is a relative dearth of strategies for the efficient generation of more structurally diverse macrocycle collections in which there is greater variation in the nature of macrocyclic scaffolds present. Such macrocycle collections should contain compounds with a broad range of biological activities (including antibacterial activities) and the requisite robust synthetic methodology useful for analogue synthesis and lead optimization once an active compound has been identified in a biological screen. Herein, we describe a new and expedient diversity-oriented synthesis (DOS) strategy for the generation of a library of novel structurally diverse macrocyclic compounds with a high level of scaffold diversity. The strategy is concise, proceeds from readily-available starting materials, is modular in nature and features a variety of macrocyclisation techniques. In this proof-of-concept study, the synthesis of several previously unreported macrocyclic compounds was achieved. Each of these macrocycles was based around a distinct molecular scaffold and contained natural product-like structural features (e.g., three-dimensionality and multiple hydrogen bond donors and acceptors) as well as synthetic handles for potential further elaboration. The successful generation of these macrocycles demonstrates the feasibility of the new DOS strategy as a synthetic platform for library generation.
4? Participation of 1-Aza-1,3-butadienes in Cycloaddition Reactions: Intramolecular Diels-Alder Reactions of α,β-Unsaturated N-Sulfonylimines
Boger, Dale L.,Corbett, Wendy L.
, p. 2068 - 2074 (1993)
The 4? participation of α,β-unsaturated N-sulfonylimines in intramolecular Diels-Alder reactions with unactivated dienophiles is detailed in studies which further extend the scope of the cycloaddition reactions of this new class of 1-aza-1,3-butadienes.Similar to observations made in the intermolecular cycloaddition reactions, a strong endo diastereoselectivity (>20:1) was observed to dominate in the cycloaddition reaction of 5b versus 5a and 5c.This endo specific reaction may be attributed to the combination of a pronounced, stabilizing secondary orbital interaction and preferred cycloaddition through an anti-endo transition state in which the lone pair on nitrogen and the C-aryl bond of the dienophile lie trans periplanar to one another benefiting from stabilization analogous to the ground-state anomeric effect.
Intramolecular allyl transfer reaction from allyl ether to aldehyde groups: Experimental and theoretical studies
Franco, Delphine,Wenger, Karine,Antonczak, Serge,Cabrol-Bass, Daniel,Dunach, Elisabet,Rocamora, Merce,Gomez, Montserrat,Muller, Guillermo
, p. 664 - 672 (2002)
The intramolecular transfer of the allyl group of functionalized allyl aryl ethers to an aldehyde group in the presence of Ni0 complexes was studied from chemical, electrochemical and theoretical points of view. The chemical reaction involves the addition of Ni0 to the allyl ether followed by stoichiometric allylation. The electrochemical process is catalytic in nickel and involves the reduction of intermediate η3-allylnickel(II) complexes.
MACROCYCLIC COMPOUNDS USEFUL AS CHITINASE INHIBITORS
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Paragraph 0127; 0180-0181; 0193, (2021/07/29)
The present invention relates to macrocyclic compounds of formula (I) and their use as chitinase inhibitors as well as to pharmaceutical compositions and methods of preparation thereof. The compounds can in particular be used in the treatment, prevention and/or amelioration of asthma.
Discovery of seneciobipyrrolidine derivatives for the amelioration of glucose homeostasis disorders through 4E-BP1/Akt/AMPK signaling activation
Che, Jinxin,Chen, Binhui,Dong, Xiaowu,Gan, Lishe,Hu, Yongzhou,Jin, Xinxin,Li, Jingya,Lu, Jialiang,Ma, Canliang,Shi, Qiuqiu,Song, Rui,Xu, Fan
, (2021/11/16)
Modulating the glucose transport in skeletal muscle is a promising strategy for ameliorating glucose homeostasis disorders. However, the complicated mechanisms of glucose transport make it difficult to find compounds therapeutically relevant molecular mechanisms of action, while phenotypic screening is thought to be an alternative approach to mimic the cell state of interest. Here, we report (±)-seneciobipyrrolidine (1a) is first found to enhance glucose uptake in L6 myotubes through phenotype-based screening. Further SAR investigation led to the identfication of compound A27 (EC50 = 2.7 μM). Proteomiic analysis discloses the unique function mechanism of A27 through upregulating the level of the eukaryotic translation initiation factor 4E-binding protein 1 (4E-BP1), subsequently enhancing the Akt and AMPK phosphorylation, thereby promoting the glucose uptake. Chronic oral administration of A27 significantly lowers blood glucose and improves glucose tolerance in db/db mice. This work is new research on seneciobipyrrolidine derivatives, providing a promising avenue for ameliorating glucose homeostasis.
SUBSTITUTED CHROMANES, ANALOGS THEREOF, AND METHODS OF USE AND SYNTHESIS
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Paragraph 0162; 0185-0186, (2021/01/25)
Disclosed are chromane compounds, analogs thereof, and methods of their synthesis and use. The compounds may be synthesized by methods involving reductive annulations of arylidene malonates with unsaturated electrophiles using photoredox/Lewis acid cooperative catalysis. The compounds may be formulated in a pharmaceutical composition for treating one of the aforementioned diseases or disorders.
tert-Butyl Hydroperoxide-Initiated Radical Cyclization of 1-(Allyloxy)-2-(1-Arylvinyl)Benzenes with Sulfinic Acids to Access Sulfonated Benzoxepines
Kuang, Kaimo,Wu, Meixia,Wu, Sixin,Xia, Ziqin,Xu, Qiankun,Zhang, Man,Zhou, Nengneng
supporting information, p. 3491 - 3495 (2021/06/28)
A tert-butyl hydroperoxide-initiated radical cyclization of 1-(allyloxy)-2-(1-arylvinyl)benzenes with sulfinic acids for the construction of sulfonated benzoxepines is developed. This reaction involves a radical pathway and offers a straightforward route to the formation of seven-membered ring via sulfonylation/cyclization process. This methodology features mild reaction conditions, a broad substrate scope and good functional group tolerance. (Figure presented.).
CHEMOSENSOR AND A METHOD OF DETECTING PALLADIUM IONS
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Paragraph 0046; 0149, (2020/12/25)
A palladium selective chemosensor based on a fluorescein-allyloxy benzene scaffold and a method of detecting palladium ions in a fluid sample with the chemosensor, whereby the fluid sample is contacted with a solution that includes water and the chemosensor to form a mixture. An ultraviolet visible absorption profile and/or a fluorescence emission profile of the mixture is measured to determine a presence or absence of palladium ions in the fluid sample, wherein the chemosensor has an ultraviolet visible absorption peak at 315 to 325 nm and a fluorescence emissions peak at 380 to 400 nm in the solution, and wherein a bathochromic shift in the ultraviolet visible absorption peak to 338 to 342 nm in the mixture and/or a bathochromic shift in the fluorescence emissions peak to 530 to 550 nm in the mixture indicates the presence of palladium ions in the fluid sample.
Highly regioselective O-allylation of phenol derivatives using MMZCu(I)Y catalyst
Thangapriya, Cheirmakani,Ilaamirthamani, Simsonrubarathinam,Kumarraja, Mayilvasagam
, p. 361 - 367 (2019/12/11)
A clean and effective method has been developed for the regioselective of O-allylation of phenol derivatives using a recyclable Cu(I)-exchanged multi-size porous material. Ease of preparation of catalyst through simple solid-state exchange and its compatibility in producing excellent amount of O-allylated products and a plausible mechanistic pathway for the regioselectivity are highlighted. This reported procedure is not requiring any external stabilizing ligand for Cu(I) species and further purification of products.
