52010-97-6Relevant articles and documents
Novel Meta-iodobenzylguanidine-Based Copper Thiosemicarbazide-1-guanidinomethylbenzyl Anticancer Compounds Targeting Norepinephrine Transporter in Neuroblastoma
Zhang, Haiyuan,Xie, Fang,Cheng, Muhua,Peng, Fangyu
, p. 6985 - 6991 (2019)
Meta-iodobenzylguanidine (MIBG) is a ligand with high affinity against norepinephrine transporter (NET) that has been used for diagnostic imaging and radionuclide therapy of NET-expressing tumors, such as neuroblastoma. We hypothesize that MIBG can be used as a ligand for development of new anticancer drugs targeting NET-expressing neuroblastoma (NB). To test our hypothesis, we synthesized two MIBG-based anticancer copper complexes [Cu(m-TSBG)2 and Cu(p-TSBG)2] by conjugation of a thiosemicarbazone copper group onto MIBG ligand. Both Cu(m-TSBG)2 and Cu(p-TSBG)2 compounds showed potent anticancer activity against NB cells (BE2C and SK-N-DZ cells). The NB-specific anticancer activity of Cu(m-TSBG)2 and Cu(p-TSBG)2 was further demonstrated by the reduced anticancer activities when nonconjugated MIBG ligand was used to competitively block binding of Cu(m-TSBG)2 or Cu(p-TSBG)2 onto NET-expressing NB cells. Both Cu(m-TSBG)2 or Cu(p-TSBG)2 compounds hold potential as promising new drugs for targeted therapy of neuroblastoma and other NET-expressing tumors.
IBX oxidation of benzenedimethanols in the presence of cucurbit[8]uril
Cong, Hang,Chen, Qiuju,Geng, Qingxia,Tao, Zhu,Yamato, Takehiko
, p. 545 - 549 (2015)
The cucurbit[8]uril (Q[8]) mediated oxidation of benzenedimethanols with o-iodoxybenzoic acid (IBX) in aqueous solution has been investigated, and the results reveal the supramolecular catalysis depends on the electronic and geometric structure of substrate. In the cases of o-benzenedimethanol (1a) and m-benzenedimethanol (1b), the IBX oxidation could be obviously enhanced by the addition of Q[8] at different extent. There is no observation of the catalytic activity of Q[8] when p-benzenedimethanol (1c) is subjected to the IBX oxidation. The addition amount of Q[8] is discussed herein, and the addition of more than 10% mol catalyst cannot improve the oxidation much more. The investigation of host-guest interactions by isothermal titration calorimetry implies the supramolecular catalysis is related to the formation of complexes between benzenedimethanols and cucurbit[8]uril. The supramolecular catalysis of Q[8] (cucurbit[8]uril) on the IBX (o-iodoxybenzoic acid) oxidation of o,m,p-benzenedimethanols in aqueous solvent and the host-guest interactions have been investigated.
Biomass-derived phosphorus-doped carbon materials as efficient metal-free catalysts for selective aerobic oxidation of alcohols
Hu, Xiwei,Fan, Mengying,Zhu, Yangyang,Zhu, Qian,Song, Qiang,Dong, Zhengping
, p. 5274 - 5283 (2019)
Heteroatom-doped carbon materials (HDCMs) with abundant active functional groups and stable structural characteristics are promising catalysts for eco-friendly metal-free catalysis. In this work, phosphorus-doped carbon materials with a highly porous structure and extremely high surface area (>1600 m2 g-1) were successfully prepared via a convenient and scalable strategy using easily available soluble starch and phosphoric acid, which are expected to show good performance in mass-transfer and thus promote the catalytic process. As expected, the as-prepared PC-700 catalyst showed remarkable catalytic performance in aerobic oxidation of benzyl alcohol with a higher TOF value than other previously reported heteroatom-doped carbon catalysts. It also exhibited great tolerance for various substrates, including aromatic, alicyclic, heterocyclic, and aliphatic alcohols. On the basis of the related characterization studies and experimental results, it was proved that the P-O-C species and the defects caused by P-O species doping in the PC-700 catalyst are the active sites for aerobic oxidation. A unique mechanism was proposed for the catalytic process, which is different from that of N-doped graphene and graphene oxide catalyzed reactions that follow a free radical mechanism. In addition, the recycling test and characterization of the reused catalyst indicate that the PC-700 shows extraordinary performance in terms of both recyclability and stability and retains high reactivity even after eight cycles.
Synthesis and characterization of complexes imparting N-pyridyl bonded meso-pyridyl substituted dipyrromethanes
Yadav, Mahendra,Singh, Ashish Kumar,Pandey, Rampal,Pandey, Daya Shankar
, p. 841 - 849 (2010)
The meso-pyridyl substituted dipyrromethane ligands 5-(4-pyridyl)dipyrromethane (4-dpmane) and 5-(3-pyridyl)dipyrromethane (3-dpmane) have been employed in the synthesis of a series of complexes with the general formulations [(η6-arene)RuCl2(L)] (η6-arene = C6H6, C10H14) and [(η5-C5Me5)MCl2(L)] (M = Rh, Ir). The reaction products have been characterized by microanalyses and spectral studies and molecular structures of the complexes [(η6-C10H14)RuCl2(4-dpmane)] and [(η5-C5Me5)IrCl2(3-dpmane)] have been determined crystallographically. For comparative studies, geometrical optimization have been performed on the complex [(η5-C5Me5)IrCl2(4-dpmane)] using exchange correlation functional B3LYP. Optimized bond length and angles are in good agreement with the structural data of the complex [(η5-C5Me5)IrCl2(3-dpmane)]. The complexes [(η6-C10H14)RuCl2(3-dpmane)], [(η5-C5Me5)RhCl2(3-dpmane)] and [(η5-C5Me5)IrCl2(3-dpmane)] have been employed as a transfer hydrogenation catalyst in the reduction of aldehydes. It was observed that the rhodium and iridium complexes mentioned above are more effective in this regard in comparison to the ruthenium complex.
Synthesis of Oxasmaragdyrin–Amino Acid Conjugates
Laxman, Kandala,Ravikanth, Mangalampalli
, p. 5884 - 5891 (2017)
A series of covalently linked oxasmaragdyrin-amino acid and BF2-oxasamaragdyrin–amino acid conjugates were synthesized by treating oxasmaragdyrin or its BF2 complex that contain a benzylhydroxyl group at one of the meso positions with an appropriate fluorenylmethyloxycarbonyl-protected amino acid in CH2Cl2 in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide·HCl/hydroxybenzotriazole under basic conditions at room temperature. The conjugates are stable, highly soluble in all organic solvents, and confirmed by HRMS. 1D and 2D NMR spectroscopic techniques were used to characterize the oxasmaragdyrin–amino acid conjugates. Absorption, fluorescence, and electrochemical studies of conjugates indicate that the conjugates strongly absorb and emit in visible-NIR region with decent quantum yields, singlet state lifetimes and are stable under electrochemical conditions. Furthermore, the conjugates showed minimal change in their spectral and electrochemical properties relative to that of the unconjugated oxasmaragdyrin or its BF2 complex suggest that the characteristic features of the oxasmaragdyrin and its BF2 complex is retained in the conjugates, which will be a useful feature for Near-IR fluorescence imaging and other applications.
One-pot synthesis and PEGylation of hyperbranched polyacetals with a degree of branching of 100%
Liu, Na,Vignolle, Joan,Vincent, Jean-Marc,Robert, Frederic,Landais, Yannick,Cramail, Henri,Taton, Daniel
, p. 1532 - 1542 (2014)
The Bronsted acid-catalyzed polytransacetalization of hydroxymethylbenzaldehyde dimethylacetal (1), a commercially available AB 2-type monomer, led to hyperbranched polyacetals (HBPA's) with a degree of branching (DB) around 0.5 by forming methanol as byproduct. In sharp contrast, the polyacetalization of the nonprotected homologue, namely, hydroxymethylbenzaldehyde (2), yielded HBPA's with DB = 1, by forming water as byproduct, under the same acidic conditions. This major difference arises from the instability of the initially formed hemiacetal intermediates, which react faster than aldehyde moieties, driving the polyacetalization toward the quantitative formation of dendritic acetal units. This represents a rare example of defect-free hyperbranched polymer synthesis utilizing a very simple AB 2-type monomer. Bronsted acid catalysts included p-toluenesulfonic, camphorsulfonic, and pyridinium camphorsulfonic acids. Trapping of the water generated during polyacetalization of 2 was accomplished using molecular sieves regularly renewed, which allowed achieving polymers of relatively high molar masses. These HBPA's with DB = 1 featuring multiple aldehyde functions at their periphery were further derivatized into PEGylated HBPA's, using linear amino-terminated poly(ethylene oxide)s of different molar masses. This led to submicrometric sized HBPA's with a core-shell architecture. Finally, HBPA derivatives could be readily hydrolyzed under acidic conditions (e.g., pH = 4), owing to the acid sensitivity of their constitutive acetal linkages.
Application of bioorthogonal hetero-Diels-Alder cycloaddition of 5-arylidene derivatives of 1,3-dimethylbarbituric acid and vinyl thioether for imaging inside living cells
Bazan, Bart?omiej,Pa?asz, Aleksandra,Skalniak, ?ukasz,Cie?, Dariusz,Buda, Szymon,J?drzejowska, Katarzyna,G?omb, Sonia,Kamzol, Daniel,Czarnota, Kinga,Latos, Krystian,Kozie?, Krzysztof,Musielak, Bogdan
supporting information, p. 6045 - 6058 (2021/07/25)
New bioorthogonal cycloaddition of 5-arylidene derivatives of 1,3-dimethylbarbituric acid as 1-oxa-1,3-butadienes and vinyl thioether as a dienophile has been applied to imaging inside living cells. The reaction is high yielding, selective, and fast in aqueous media. The proposed 1-oxa-1,3-butadiene derivative conjugated to a FITC fluorochrome selectively and rapidly labels the cancer cells pretreated with the dienophile-taxol. The second order rate constants k2 for various proposed bioorthogonal cycloadditions were estimated to be in the range from 0.9 × 10-2 M-1 s-1 to 1.4 M-1 s-1, which is much better than in the case of the first generation TQ-ligation (o-quinolinone quinone methide and vinyl thioether ligation, k2 = 1.5 × 10-3 M-1 s-1) and comparable or better to that for the second generation TQ-ligation (k2 = 2.8 × 10-2 M-1 s-1). The reaction rate constants k2 of proposed ligation reactions are in the range of the rate constants k2 for tetrazines and norbornenes or tetrazines and cyclopropenes. These findings indicate that this chemistry is suitable for in vitro imaging experiments.
Efficient and chemoselective hydrogenation of aldehydes catalyzed by well-defined PN3-pincer manganese(ii) catalyst precursors: An application in furfural conversion
Gholap, Sandeep Suryabhan,Dakhil, Abdullah Al,Chakraborty, Priyanka,Li, Huaifeng,Dutta, Indranil,Das, Pradip K.,Huang, Kuo-Wei
supporting information, p. 11815 - 11818 (2021/11/30)
Well-defined and air-stable PN3-pincer manganese(ii) complexes were synthesized and used for the hydrogenation of aldehydes into alcohols under mild conditions using MeOH as a solvent. This protocol is applicable for a wide range of aldehydes containing various functional groups. Importantly, α,β-unsaturated aldehydes, including ynals, are hydrogenated with the CC double bond/CC triple bond intact. Our methodology was demonstrated for the conversion of biomass derived feedstocks such as furfural and 5-formylfurfural to furfuryl alcohol and 5-(hydroxymethyl)furfuryl alcohol respectively.
Histone deacetylase inhibitor as well as preparation and application thereof
-
Paragraph 0042-0043, (2021/04/28)
The invention relates to a histone deacetylase inhibitor and preparation and an application thereof, in particular to a novel histone deacetylase inhibitor based on a beta-elemene structure and a preparation method thereof, and further relates to an intermediate for synthesizing the histone deacetylase inhibitor and a preparation method thereof. The invention also relates to an application of the histone deacetylase inhibitor in preparation of antitumor drugs, and belongs to the technical field of chemical synthesis of drugs. The zinc ion combined compound and the salt or solvate thereof are shown as a general formula (I) or (II), wherein R, X, n and i are described in the claims and the specification.
Synthesis and evaluation of novel α-aminoamides containing benzoheterocyclic moiety for the treatment of pain
Cheng, Jingchao,He, Junlin,Ren, Fengxia,Ren, Fengzhi,Shi, Weiguo,Tong, Kun,Yu, Zixing,Zhang, Ruotian,Zhang, Tao,Zhang, Yatong
, (2021/06/15)
Novel α-aminoamide derivatives containing different benzoheterocyclics moiety were synthesized and evaluated as voltage-gated sodium ion channels blocks the treatment of pain. Compounds 6a, 6e, and 6f containing the benzofuran group displayed more potent in vivo analgesic activity than ralfinamide in both the formalin test and the writhing assay. Interestingly, they also exhibited potent in vitro anti-Nav 1.7 and anti-Nav 1.8 activity in the patch-clamp electrophysiology assay. Therefore, compounds 6a, 6e, and 6f, which have inhibitory potency for two pain-related Nav targets, could serve as new leads for the development of analgesic medicines.
