72758-79-3Relevant academic research and scientific papers
Borane-Catalyzed, Chemoselective Reduction and Hydrofunctionalization of Enones Enabled by B-O Transborylation
Nicholson, Kieran,Langer, Thomas,Thomas, Stephen P.
supporting information, p. 2498 - 2504 (2021/04/13)
The use of stoichiometric organoborane reductants in organic synthesis is well established. Here these reagents have been rendered catalytic through an isodesmic B-O/B-H transborylation applied in the borane-catalyzed, chemoselective alkene reduction and formal hydrofunctionalization of enones. The reaction was found to proceed by a 1,4-hydroboration of the enone and B-O/B-H transborylation with HBpin, enabling catalyst turnover. Single-turnover and isotopic labeling experiments supported the proposed mechanism of catalysis with 1,4-hydroboration and B-O/B-H transborylation as key steps.
Synthesis, Crystal Structure, and Photophysical Properties of 4-(4-(Dimethylamino)phenyl)-6-phenylpyrimidin-2-amine
Aguilar, Luis F.,Bravo, Manuel A.,Fuentealba, Mauricio,Mellado, Marco,Sánchez-González, Rodrigo,Sariego-Kluge, Rafaela,Valdés-Navarro, Franco
, (2020/10/06)
The pyrimidine core is present in a wide variety of compounds that show interesting fluorescent properties and have been used as pigments and dyes. In this research, we synthesized 4-(4-(dimethylamino)phenyl)-6-phenylpyrimidin-2-amine (compound 9) from ch
Inhibition of Caco-2 and MCF-7 cancer cells using chalcones: synthesis, biological evaluation and computational study
Aguilar, Luis F.,Coddou, Claudio,Jara-Gutierrez, Carlos,Mellado, Marco,Reyna-Jeldes, Mauricio,Villena, Joan,Weinstein-Oppenheimer, Caroline
supporting information, (2021/10/02)
Cancer is the second death cause worldwide, with breast and colon cancer among the most prevalent types. Traditional treatment strategies have several side effects that inspire the development of novel anticancer agents derived from natural sources, like chalcone derivatives. For this investigation, twenty-three chalcones (4a-w) were synthesized and evaluated as antiproliferative agents against MCF-7 and Caco-2 cells, finding three and two compounds with similar or higher antiproliferative activity than daunorubicin, while only two chalcones showed better selectivity indexes than daunorubicin on MCF-7. From these results, we developed good-performance QSAR models (r > 0.850, q2>0.650), finding several structural features that could modify chalcone activity and selectivity. According to these models, chalcones 4w and 4t have high potency and selectivity against Caco-2 and MCF-7, respectively, which make them attractive candidates for hit-to-lead development of ROS-independent pro apoptotic agents.
Synthesis, characterization and biological evaluation of new 3,5-disubstituted-pyrazoline derivatives as potential anti-Mycobacterium tuberculosis H37Ra compounds
Azmi, Mohamad Nurul,Che Omar, Mohammad Tasyriq,Osman, Hasnah,Parumasivam, Thaigarajan,Supratman, Unang,Wong, Kok Tong
, (2021/05/29)
A total of fourteen pyrazoline derivatives were synthesized through cyclo-condensation reactions by chalcone derivatives with different types of semicarbazide. These compounds were characterized by IR, 1D-NMR (1H, 13C and Distortionless Enhancement by Polarization Transfer-DEPT-135) and 2D-NMR (COSY, HSQC and HMBC) as well as mass spectroscopy analysis (HRMS). The synthesized compounds were tested for their antituberculosis activity against Mycobacterium tuberculosis H37Ra in vitro. Based on this activity, compound 4a showed the most potent inhibitory activity, with a minimum inhibitory concentration (MIC) value of 17 μM. In addition, six other synthesized compounds, 5a and 5c–5g, exhibited moderate activity, with MIC ranges between 60 μM to 140 μM. Compound 4a showed good bactericidal activity with a minimum bactericidal concentration (MBC) value of 34 μM against Mycobacterium tuberculosis H37Ra. Molecular docking studies for compound 4a on alpha-sterol demethylase was done to understand and explore ligand– receptor interactions, and to hypothesize potential refinements for the compound.
Fluorescent Molecular Logic Gates Driven by Temperature and by Protons in Solution and on Solid
West, Matthew E. S.,Yao, Chao-Yi,Melaugh, Gavin,Kawamoto, Kyoko,Uchiyama, Seiichi,de Silva, A. Prasanna
supporting information, p. 13268 - 13274 (2021/08/06)
Temperature-driven fluorescent NOT logic is demonstrated by exploiting predissociation in a 1,3,5-trisubstituted Δ2-pyrazoline on its own and when grafted onto silica microparticles. Related Δ2-pyrazolines become proton-driven YES an
Cascade Reaction of α, β-Unsaturated Ketones and 2-Aminoaryl Alcohols for the Synthesis of 3-Acylquinolines by a Copper Nanocatalyst
Liu, Yuan,Wang, Chen,Tong, Yixin,Ling, Yong,Zhou, Changjian,Xiong, Biao
supporting information, p. 4422 - 4429 (2021/08/07)
3-Acylquinolines possess widespread applications in functional chemicals. However, the convenient and selective synthesis of such important substructures has to date remained a challenge. Herein, we report a method to access 3-acylquinolines from α, β-unsaturated ketones and 2-aminoaryl alcohols in one pot with a copper nanocatalyst supported on nitrogen-silica-doped carbon (Cu/N?SiO2?C). Mechanistically, the construction of the product involves a cascade procedure including radical-type oxidation of 2-aminoaryl alcohols, aza-Michael addition and annulation. This developed protocol proceeds with merits of mild reaction conditions, good functional group tolerance, earth-abundant and reusable copper catalyst, easily available stocks and O2 as the sole oxidant, which provides an alternative way for the sustainable synthesis of quinoline derivatives. (Figure presented.).
Zinc-coordinated aza-pyrrolidone optical diagnosis and treatment reagent with long-wave absorption characteristic as well as preparation and application thereof
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Paragraph 0065-0069, (2021/06/23)
The invention discloses a zinc-coordinated aza-pyrrolidone optical diagnosis and treatment reagent with a long-wave absorption characteristic as well as preparation and application thereof. The optical diagnosis and treatment reagent is composed of a metal center and an aza-pyrrolidone auxiliary ligand; the whole preparation process is simple, the prepared complex has a long absorption wavelength, and the absorption wavelength can be prolonged along with the change of the aza-pyrrolidone auxiliary ligand, so that the optical diagnosis and treatment reagent has a deep tissue penetration depth in the field of living body application; the complex can be excited by near-infrared light and can emit near-infrared light, so that the damage of an excitation light source to a biological sample can be weakened; and the complex can be used in the field of photodynamic and photothermal combined therapy guided by biological imaging, and has an important application prospect.
Silver-coordinated aza-pyrrolidone complex, and preparation method and application thereof
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Paragraph 0036-0039, (2021/07/08)
The invention discloses a silver-coordinated aza-pyrrolidone complex, and a preparation method and application thereof. The complex is composed of an aza-pyrrolidone ligand, a silver metal center and a triphenylphosphine auxiliary ligand, the raw materials are relatively cheap, and the synthesis method is simple; and the prepared complex shows relatively strong absorption in an ultraviolet region and a near-infrared region, and can be excited by near-infrared light, so that the damage of an excitation light source to a biological sample can be weakened, and the complex has relatively deep tissue penetration depth in the field of living body application, and is more suitable for biological imaging and deep photodynamic photo-thermal combined treatment.
Pyrazoline analogs as potential anticancer agents and their apoptosis, molecular docking, MD simulation, DNA binding and antioxidant studies
Rana, Manish,Arif, Rizwan,Khan, Faez Iqbal,Maurya, Vikas,Singh, Raja,Faizan, Md Imam,Yasmeen, Shama,Dar, Sajad Hussain,Alam, Raquib,Sahu, Ankita,Ahmad, Tanveer,Rahisuddin
, (2021/02/12)
N-formyl pyrazoline derivatives (3a–3l) were designed and synthesized via Michael addition reaction through cyclization of chalcones with hydrazine hydrate in presence of formic acid. The structural elucidation of N-formyl pyrazoline derivatives was carri
α-Trifluoromethyl Chalcones as Potent Anticancer Agents for Androgen Receptor-Independent Prostate Cancer
Goto, Masuo,Izumi, Kouji,Mizokami, Atsushi,Naito, Renato,Nakagawa-Goto, Kyoko,Saito, Yohei
, (2021/05/29)
α-Trifluoromethyl chalcones were prepared and evaluated for their antiproliferative activities against androgen-independent prostate cancer cell lines as well as five additional types of human tumor cell lines. The most potent chalcone 5 showed superior antitumor activity in vivo with both oral and intraperitoneal administration at 3 mg/kg. Cell-based mechanism of action studies demonstrated that 5 induced cell accumulation at sub-G1 and G2/M phases without interfering with microtubule polymerization. Furthermore, several cancer cell growth-related proteins were identified by using chalcone 5 as a bait for the affinity purification of binding proteins.
