70-55-3Relevant articles and documents
Cellular AND Gates: Synergistic Recognition to Boost Selective Uptake of Polymeric Nanoassemblies
Fernandez, Ann,Gao, Jingjing,Thayumanavan, S.,Wu, Peidong,Zhuang, Jiaming
, p. 10456 - 10460 (2020)
The development of nanoparticle-based biomedical applications has been hampered due to undesired off-target effects. Herein, we outline a cellular AND gate to enhance uptake selectivity, in which a nanoassembly–cell interaction is turned on, only in the concurrent presence of two different protein functions, an enzymatic reaction (alkaline phosphatase, ALP) and a ligand–protein (carbonic anhydrase IX, CA IX) binding event. Selective uptake of nanoassemblies was observed in cells that overexpress both of these proteins (unicellular AND gate). Interestingly, selective uptake can also be achieved in CA IX overexpressed cells, when cocultured with ALP overexpressed cells, where the nanoassembly presumably acts as a mediator for cell–cell communication (bicellular AND gate). This logic-gated cellular uptake could find use in applications such as tumor imaging or theranostics.
Synthesis of 8-Alkoxy-5 H-isochromeno[3,4- c]isoquinolines and 1-Alkoxy-4-arylisoquinolin-3-ols through Rh(III)-Catalyzed C-H Functionalization of Benzimidates with 4-Diazoisochroman-3-imines and 4-Diazoisoquinolin-3-ones
Li, Zhenmin,Lu, Ping,Wang, Yanguang,Xie, Jianwei
, p. 5525 - 5535 (2020)
Rh(III)-catalyzed C-H activation/annulation of benzimidates with 4-diazoisochroman-3-imines furnished 8-alkoxy-5H-isochromeno[3,4-c]isoquinolines in moderate to excellent yields with a broad range of substrate scope. The reaction was carried out under mild reaction conditions and could be scaled up with practical usage. Similar reaction between benzimidates and 4-diazoisoquinolin-3-ones provided 1-alkoxy-4-arylisoquinolin-3-ols in excellent yields. Moreover, the synthesized products could be conveniently transformed to the corresponding heterocycles with a 1,8-naphthyridinone or isochromenopyridinone core, which are privileged structures in medicinal chemistry.
Anisole alkylation with N-arenesulfonylimines of dichloro(phenyl)acetaldehyde and derivatives thereof
Drozdova,Mirskova
, p. 819 - 821 (2001)
N-[1-4-Methoxyphenyl-2-phenyl-2,2-dichloroethyl]arenesulfonamides are formed in reaction of N-(2-phenyl-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide and N-(2-phenyl-2,2-dichloroethylidene)-4-methylbenzenesulfonamide with anisole catalyzed by boron t
Structural, vibrational spectra and normal coordinate analysis for two tautomers of 4(5)-(2′-furyl)-imidazole
Ledesma,Zinczuk,Gonzalez, J.J. Lopez,Altabef, A. Ben,Brandan
, p. 587 - 597 (2010)
We have synthesized both the 4 and 5 tautomeric forms of 4(5)-(2′-furyl)-imidazole (1) and investigated their molecular vibrations by infrared and Raman spectroscopies as well as by calculation based on the density functional theory (DFT) approach. Examination of the temperature dependence of IR intensity revealed the band characteristics of the 4 and 5 tautomersof(1).Comparisonofexperimentalandcalculatedchemicalshiftsinnucl earmagneticresonance(NMR)spectroscopy was made in order to identify the two tautomeric forms. The assignment of vibrational normal modes was performed, and the forcefieldobtainedreproduced theexperimentalvibrationalwavenumbers with a root mean-squaredeviation (RMSD)value of ca. 13 cm-1 for both tautomers. The natural bond orbital (NBO) study reveals the characteristics of the electronic delocalization of the two tautomeric structures.
Formation and Isolation of the Disulphide Dication of 1,5-Dithiacyclo-octane in the Reactions of the Corresponding S-Oxide and S-(N-tosylimide) in Concentrated Sulphuric Acid
Furukawa, Naomichi,Kawada, Akira,Kawai, Tsutomu
, p. 1151 - 1152 (1984)
The disulphide dication of 1,5-dithiacyclo-octane was generated in the reaction of the corresponding S-oxide and S-(N-tosylimide) with conc.H2SO4 and isolated in crystalline form.
Cyclopropyl aziridines: Solvolytic reactions of the N-tosylaziridines of (+)-2-carene and (+)-3-carene
Silverberg, Lee J.,Rabb, Javon M.,Reno, Joseph M.,He, Gang
, p. 193 - 199 (2014)
The N-tosylaziridine 4 of (+)-2-carene 1 was prepared and subjected to solvolytic reactions with weak protic acids. For comparison, the solvolytic reactions of cis-3-carene-N-tosylaziridine 8 were also studied. The solvolyses of 4 were more rapid than those of 8, and both rings were opened in 4, whereas only the aziridine was opened in 8. This leads to the conclusion that the aziridine and cyclopropane rings in 4 can achieve a conjugated transition state.
Data-Driven Identification of Hydrogen Sulfide Scavengers
Yang, Chun-tao,Wang, Yingying,Marutani, Eizo,Ida, Tomoaki,Ni, Xiang,Xu, Shi,Chen, Wei,Zhang, Hui,Akaike, Takaaki,Ichinose, Fumito,Xian, Ming
, p. 10898 - 10902 (2019)
Hydrogen sulfide (H2S) is an important signaling molecule whose up- and down-regulation have specific biological consequences. Although significant advances in H2S up-regulation, by the development of H2S donors, have been achieved in recent years, precise H2S down-regulation is still challenging. The lack of potent/specific inhibitors for H2S-producing enzymes contributes to this problem. We expect the development of H2S scavengers is an alternative approach to address this problem. Since chemical sensors and scavengers of H2S share the same criteria, we constructed a H2S sensor database, which summarizes key parameters of reported sensors. Data-driven analysis led to the selection of 30 potential compounds. Further evaluation of these compounds identified a group of promising scavengers, based on the sulfonyl azide template. The efficiency of these scavengers in in vitro and in vivo experiments was demonstrated.
Fine-tuning hydroxylamines as single-nitrogen sources for Pd(0)-catalyzed diamination of o-bromo(or chloro)-biaryls
Bai, Jiaxing,Ding, Pin,Han, Lingbo,Liu, Jingjing,Luan, Xinjun
, (2022/03/19)
Transition metal-catalyzed diamination by hydroxylamines is a common approach for making three-membered aziridines, while its use for building the larger N-heterocycles is still underdeveloped. Herein, we report an efficient Pd(0)-catalyzed inter-molecular [4+1] annulation of o-bromo(or chloro)-biaryls with bifunctional secondary hydroxylamines for the one-step assembly of synthetically useful carbazoles. Noteworthily, a linchpin for this domino reaction was the judicious selection of both the amino-sources and Pd(0)-catalysts for enabling the prerequisite oxidative addition of aryl halides to Pd(0)-species in the presence of hydroxylamines with a labile N-O bond. [Figure not available: see fulltext.].
Synthesis, biological evaluation, and docking studies of novel pyrrolo[2,3-b]pyridine derivatives as both ectonucleotide pyrophosphatase/phosphodiesterase inhibitors and antiproliferative agents
Ullah, Saif,El-Gamal, Mohammed I.,El-Gamal, Randa,Pelletier, Julie,Sévigny, Jean,Shehata, Mahmoud K.,Anbar, Hanan S.,Iqbal, Jamshed
, (2021/03/22)
Ecto-nucleotide pyrophosphatases/phosphodiesterases (NPPs) together with nucleoside triphosphate diphosphohydrolases (NTPDases) and alkaline phosphatases (APs) are nucleotidases located at the surface of the cells. NPP1 and NPP3 are important members of NPP family that are known as druggable targets for a number of disorders such as impaired calcification, type 2 diabetes, and cancer. Sulfonylurea derivatives have been reported as antidiabetic and anticancer agents, therefore, we synthesized and investigated series of sulfonylurea derivatives 1a-m possessing pyrrolo[2,3-b]pyridine core as inhibitors of NPP1 and NPP3 isozymes that are over-expressed in cancer and diabetes. The enzymatic evaluation highlighted compound 1a as selective NPP1 inhibitor, however, 1c was observed as the most potent inhibitor of NPP1 with an IC50 value of 0.80 ± 0.04 μM. Compound 1l was found to be the most potent and moderately selective inhibitor of NPP3 (IC50 = 0.55 ± 0.01 μM). Furthermore, in vitro cytotoxicity assays of compounds 1a-m against MCF-7 and HT-29 cancer cell lines exhibited compound 1c (IC50 = 4.70 ± 0.67 μM), and 1h (IC50 = 1.58 ± 0.20 μM) as the most cytotoxic compounds against MCF-7 and HT-29 cancer cell lines, respectively. Both of the investigated compounds showed high degree of selectivity towards cancer cells than normal cells (WI-38). Molecular docking studies of selective and potent enzyme inhibitors revealed promising mode of interactions with important binding sites residues of both isozymes i.e., Thr256, His380, Lys255, Asn277 residues of NPP1 and His329, Thr205, and Leu239 residues of NPP3. In addition, the most potent antiproliferative agent, compound 1h, doesn't produce hypoglycemia as a side effect when injected to mice. This is an additional merit of the promising compound 1h.
Synthesis of magnetic chitosan supported metformin-Cu(II) complex as a recyclable catalyst for N-arylation of primary sulfonamides
Ahmadpoor, Fatemeh,Nasrollahzadeh, Mahmoud,Nezafat, Zahra,Pakzad, Khatereh
, (2021/06/25)
The application of chitosan, which has received much attention as a natural polymer and effective support, has many advantages such as biodegradability and biocompatibility. In this study, the immobilization of a copper complex on the magnetic chitosan bearing metformin ligand has been developed through immobilizing structurally defined metformin with long tail of (3-chloropropyl)trimethoxysilane (TMOS). The synthesized Fe3O4-chitosan@metformin-Cu(II) complex (Fe3O4-CS@Met-Cu(II)) was used as an effective, reusable and magnetic catalyst in the N-arylation of different derivatives of primary sulfonamides with arylboronic acids in ethanol. The primary sulfonamides were prepared from the reaction of sulfonyl chlorides with sodium cyanate in water under ultrasonic irradiation. Utilizing a wide variety of substrates in EtOH as a green solvent, high yields of the primary and secondary sulfonamides, easy work-up along with the excellent recovery and reusability of the catalyst, make this process a simple, economic and environmentally benign method. The synthesized Fe3O4-CS@Met-Cu(II) was characterized using various techniques such as XRD (X-ray diffraction), EDS (energy-dispersive X-ray spectroscopy), elemental mapping, TEM (transmission electron microscopy), FESEM (field emission scanning electron microscopy), VSM (vibrating sample magnetometer), ICP-MS (inductively coupled plasma mass spectroscopy), TGA (thermogravimetric analysis) and FT-IR (Fourier-transform infrared spectroscopy) analyses. The catalyst can be recycled and reused 5 times with no considerable loss of catalytic activity.