24870-11-9Relevant articles and documents
1,3-dipolar cycloaddition: Free catalytic synthesis and esophageal cancer activity of new 1,2,3-triazole-oxydianiline-maleimide hybrids
Mohammed, Mohammed K.,Almashal, Faeza A.,Jassem, Ahmed M.
, p. 47 - 53 (2021/01/18)
A new series of 1,2,3-triazole-oxydianiline-maleimide hybrids 12-15 was synthesized by using 1,3-dipolar cycloaddition reaction of N-Arylmaleimides 6-9 with 4,4'-oxybis(azidobenzene) 11 under an efficient and free catalytic reaction. All the newly synthesized hybrids were characterized by their 1H NMR, F-TIR, Mass spectral data and melting points. The cytotoxic activities (in vitro) of selected hybrids against esophageal cancer of human cell line (SKG) were evaluated by MTT assay. Among them, hybrid 13 exhibited a potent inhibition activity with the IC50 value of 1.61±0.01 μM against esophageal cancer cell (SKG). Cellular mechanism investigations in esophageal carcinoma cells (SKG) elucidated that hybrid 13 inhibited cell growths in vitro and arrested cell cycle at an environmental phase. These results revealed that hybrid 13 holds a promising anticancer agent with the enhancement of further clinical applications in drug discovery field.
Synthesis of Tetrahydroisoindolinones via a Metal-Free Dehydrogenative Diels-Alder Reaction
Xu, Wen-Lei,Tang, Lei,Ge, Chen-Yu,Chen, Jie,Zhou, Ling
supporting information, p. 2268 - 2273 (2019/04/10)
A metal-free dehydrogenative Diels-Alder reaction of substituted alkenes for the synthesis of tetrahydroisoindolinones has been exploited for the first time. This new method features functional group tolerance and broad substrate scope, providing an efficient access to biologically active tetrahydroisoindolinone skeletons with endo steroselectivity in good to excellent yields. (Figure presented.).
Synthesis and biological evaluation of novel benzylidene-succinimide derivatives as noncytotoxic antiangiogenic inhibitors with anticolorectal cancer activity in vivo
Luo, Kaixiu,Bao, Yafeng,Liu, Feifei,Xiao, Chuanfan,Li, Ke,Zhang, Conghai,Huang, Rong,Lin, Jun,Zhang, Jihong,Jin, Yi
, p. 805 - 827 (2019/07/10)
A novel series of benzylidene-succinimide derivatives were synthesized, characterized and evaluated for their cytotoxicities against HCT116, and SW480 cancer cells and NCM460 normal human cells. Their antiangiogenic capabilities were evaluated using a chick chorioallantoic membrane (CAM) assay. The compound, XCF-37b, was selected as the most potent antiangiogenic inhibitor with noncytotoxicity to evaluate the pharmacological effects on human umbilical vein endothelial cells (HUVECs) and cancer cells in vivo and in vitro. The results showed that XCF-37b inhibited HT29-cell colon tumor growth in vivo, without showing cytotoxicity against the five other cancer cell lines in vitro. Experiments confirmed that XCF-37b had obvious antiangiogenic activity by HUVEC migration and invasion and rat aortic ring angiogenesis ex vivo. Mechanism studies showed that XCF-37b inhibited the AKT/mTOR and VEGFR2 signaling pathways, as evidenced by decreased expressions of phosphor-AKT (p-AKT), p-mTOR, p-VEGFR2 (Tyr175), p-Src (Tyr416), p-FAK (Tyr925), and p-Erk1/2 (Thr202/Tyr204). Moreover, XCF-37b significantly decreased the protein expressions of matrix metalloproteinase-2 (MMP-2), MMP-9 and hypoxia-inducible factor-1α (HIF-1α). XCF-37b generally regulated angiogenic inhibition through several regulatory pathways, without significantly interfering with colorectal cancer cell growth.
A Synthetic Replicator Drives a Propagating Reaction-Diffusion Front
Bottero, Ilaria,Huck, Jürgen,Kosikova, Tamara,Philp, Douglas
supporting information, p. 6723 - 6726 (2016/06/15)
A simple synthetic autocatalytic replicator is capable of establishing and driving the propagation of a reaction-diffusion front within a 50 μL syringe. This replicator templates its own synthesis through a 1,3-dipolar cycloaddition reaction between a nit
Triethylamine-catalyzed synthesis of oxazepine from maleamic acids
Badru, Rahul,Singh, Baldev
, p. 635 - 640 (2015/05/13)
2-Thioxo-1,3-oxazepine-4,7-dione compounds were obtained via triethylamine-catalyzed condensation of maleamic acids with thiophosgene under anhydrous conditions. This method features relatively a simple methodology, use of inexpensive reagents, convenient operating conditions and high yields.
1,3-dipolar cycloaddition reactions leading to the synthesis of new 2,3,5-triaryl-4h,2,3,3a,5,6,6a-hexahydropyrrolo[3,4-d]isoxazole-4,6-diones
Kaur, Anjandeep,Singh, Baldev
, p. 1421 - 1429 (2015/04/27)
Cycloaddition of C,N-diphenylnitrones 1 to N-aryl maleimides 2 afforded two diastereomeric isoxazolidines with high selectivity. The structure and steric configuration of the adducts have been assigned on the basis of 1H NMR, 1H NMR COSY, 13C NMR and IR spectroscopy. The π-π stacking interactions between maleimide's and nitrone's aromatic rings during the 1,3-dipolar cycloaddition were assumed to control the exo-endo selectivity of the reaction. Thus, the exo-endo ratio depends upon the position of the substituent present on the C-phenyl ring of the C,N-diphenylnitrones.
One-pot regioselective synthesis of novel 1-N-methyl-spiro[2,3']oxindole-spiro[3,3"]-1"-N-arylpyrrolidine-2",5"-dione-4-arylpyrrolidines through multicomponent 1,3-dipolar cycloaddition reaction of azomethine ylide
Kaur, Anjandeep,Kaur, Manpreet,Singh, Baldev
, p. 827 - 833 (2015/05/13)
An atom economic and facile synthesis of novel dispiro-oxindole-pyrrolidines has been achieved via a three-component tandem cycloaddition of azomethine ylide generated in situ from isatin and sarcosine by decarboxylative condensation with N-aryl-3-benzylidene-pyrrolidine-2,5-dione derivatives as dipolarophiles. The salient features of synthetic procedure are characterized by the mild reaction conditions, high yields, high regioselectivity and stereoselectivity, one-pot procedure, and operational simplicity. This regioselectivity was assumed to be under the influence of π-π stacking interactions between the aromatic rings of azomethine ylide and N-aryl-3-benzylidene-pyrrolidine-2,5-diones that further control the exo-endo selectivity of the reaction 1,3-dipolar cycloaddition. The regiochemistry and structures of the cycloadducts were determined with spectroscopic data.
DABCO-catalyzed [3+2] cycloaddition reactions of azomethine imines with N-aryl maleimides: Facile access to dinitrogen-fused heterocycles
Jia, Qianfa,Chen, Lei,Yang, Gongming,Wang, Jian,Wei, Jia,Du, Zhiyun
supporting information, p. 7150 - 7153 (2015/12/12)
DABCO-catalyzed [3+2] cycloaddition of azomethine imines with maleimides has been developed. This method could efficiently furnish dinitrogen-fused tetracyclic heterocycles in high levels of regioselectivity and with good yields.
Synthesis and pharmacological evaluation of analogues of benzyl quinolone carboxylic acid (BQCA) designed to bind irreversibly to an allosteric site of the M1 muscarinic acetylcholine receptor
Davie, Briana J.,Valant, Celine,White, Jonathan M.,Sexton, Patrick M.,Capuano, Ben,Christopoulos, Arthur,Scammells, Peter J.
, p. 5405 - 5418 (2014/07/08)
Activation of the M1 muscarinic acetylcholine receptor (mAChR) is a prospective treatment for alleviating cognitive decline experienced in central nervous system (CNS) disorders. Current therapeutics indiscriminately enhance the activity of the endogenous neurotransmitter ACh, leading to side effects. BQCA is a positive allosteric modulator and allosteric agonist at the M1 mAChR that has high subtype selectivity and is a promising template from which to generate higher affinity, more pharmacokinetically viable drug candidates. However, to efficiently guide rational drug design, the binding site of BQCA needs to be conclusively elucidated. We report the synthesis and pharmacological validation of BQCA analogues designed to bind irreversibly to the M1 mAChR. One analogue in particular, 11, can serve as a useful structural probe to confirm the location of the BQCA binding site; ideally, by co-crystallization with the M1 mAChR. Furthermore, this ligand may also be used as a pharmacological tool with a range of applications.
An expeditious synthesis of imides from phthalic, maleic and succinic anhydrides and chemoselective C=C reduction of maleic amide esters
Kumar, Padam Praveen,Reddy, Y. Dathu,Kumari, Y. Bharathi,Devi, B. Rama,Dubey
, p. 392 - 398 (2014/05/06)
Phthalic, maleic and succinic anhydrides have been reacted with aromatic amines to obtain the corresponding monoacid monoamides. The latter have been each transformed into the corresponding cyclic imide derivatives by treating with SOCl2. Alternatively, anhydrides have been reacted with methanolic KOH to obtain monomethyl ester derivatives which on reaction with aromatic amines in the presence of EDC. HCl and HOBt give cyclic imide derivatives. Reaction of monoacid monoamides independently, with SOCl 2 at 0-5°C give the monoamide monoester derivatives. Treatment of monoamide monoester of malic anhydride with NaBH4 leads to the unusual reduction of C=C grouping as well as the carbonyl group of the ester group to from monoamide monoalcohol of succinic anhydride. Preparation of monoamide monoalcohol of succinic anhydride can also be achieved by chemoselective reduction of monoamide monoester of malic anhydride with Mg turnings yielding monoamide monoester of succinic anhydride followed by reduction of the latter with NaBH4.
