115846-95-2Relevant academic research and scientific papers
ACI/EG eutectic mixture mediated synthesis, characterization and: In vitro osteoblast differentiation assessment of spiropyrrolo[1,2- b] isoquinoline analogues
Periyasami, Govindasami,Arumugam, Natarajan,Rahaman, Mostafizur,Kumar, Raju Suresh,Manikandan, Muthurangan,Alfayez, Musaad A.,Premnath, Dhanaraj,Aldalbahi, Ali
, p. 16303 - 16313 (2018)
An eco-friendly acetylcholine iodide-ethylene glycol (ACI/EG) deep eutectic mixture mediated green protocol has been developed for the synthesis of hitherto unexplored multi-functionalized linear tricyclic spiropyrrolo[1,2-b]isoquinoline analogues. The effects of the synthesized compounds on the osteoblast differentiation of hBMSC-TERT cell lines were investigated and promising results were observed with significant IC50 values. In addition, molecular modeling simulations were also performed with the 3D structure of BMP-2 to reveal binding interactions and orientations of highly potent spiropyrrolo[1,2-b]isoquinoline analogues.
O-monoacyltartaric acid catalyzed enantioselective conjugate addition of a boronic acid to dienones: Application to the synthesis of optically active cyclopentenones
Sugiura, Masaharu,Kinoshita, Ryo,Nakajima, Makoto
, p. 5172 - 5175 (2014)
Enantioselective conjugate addition of styrylboronic acid to dienones was effectively catalyzed by an O-monoacyltartaric acid to afford monostyrylated products with good enantioselectivity. The RCM of the monostyrylated products using the Hoveyda-Grubbs II catalyst afforded optically active cyclopentenones, including a synthetic intermediate of the antitumor agent TEI-9826. The study shows that a diene additive such as 1,6-heptadiene or diallyl ether was essential for the RCM.
Synthesis, characterization and antichagasic evaluation of thiosemicarbazones prepared from chalcones and dibenzalacetones
da Silva, Aline Alves,Maia, Pedro Ivo da Silva,Lopes, Carla Duque,de Albuquerque, Sergio,Valle, Marcelo Siqueira
, (2021)
Chagas disease is a neglected disease, being one of the leading causes of death from infectious diseases. In view of the severity of this pathology, this work describes the synthesis of new thiosemicarbazones derived from chalcones and dibenzalacetones as potential drugs for the treatment of this disease. The structures of all compounds were elucidated by infrared (IR) and nuclear magnetic resonance (1H and 13C NMR) spectroscopies. The chalcone derived thiosemicarbazones 10-14 were tested against the intracellular amastigote form of the protozoan Trypanosoma cruzi and had their cytotoxicity assessed using LLC-MK2 cells. The compound 10 (IC50 = 12.25 μM) presented the best activity when compared with the standard drug benznidazole (IC50 = 5.64 μM).
Ss-NMR and single-crystal x-ray diffraction in the elucidation of a new polymorph of bischalcone (1e,4e)-1,5-bis(4-fluorophenyl)penta-1,4-dien-3-one
Ferreira, Lívia O. A.,Valdo, Ana Karoline S. M.,Neto, José Ant?nio Nascimento,Ribeiro, Leandro,da Silva, Jefferson R. D.,Queiroz, Luiz H. K.,Perez, Caridad N.,Martins, Felipe T.
, p. 694 - 701 (2019)
We report a new polymorph of (1E,4E)-1,5-bis(4-fluorophenyl)penta-1,4-dien-3-one, C17H12F2O. Contrary to the precedent literature polymorph with Z' = 3, our polymorph has one half molecule in the asymmetric unit
Supramolecular polymeric aggregation behavior and its impact on catalytic properties of imidazolium based hydrophilic ionic liquids
Muhammad, Shoaib,Javed, Muhammad Naveed,Ali, Firdous Imran,Bari, Ahmed,Hashmi, Imran Ali
, (2020)
Ionic Liquids (ILs) self-assemble to form supramolecular polymeric clusters/aggregates. The aggregation behavior of ILs influences its activity in the organic synthesis. However, the precise role of ILs in organic reactions is still unknown. It is, therefore, important to comprehend the supramolecular polymeric aggregation behavior of ILs. We are exploring the supramolecular polymeric aggregation behavior of ILs using Electrospray Ionization Mass Spectrometry (ESI-MS). We have synthesized four hydrophilic ILs (1–4) and investigated their aggregation behavior and its impact on catalytic activity in Carbon-Carbon bond formation (Knoevenagel and Claisen-Schmidt condensation). Here, we show that the aggregation behavior of ILs depends on the type and nature of cation and anion. ESI-MS (?ve) spectra reveals two different type of aggregation i.e. [CnAn+1]? & [A2 + H+]?. We have found that catalytic activity increases with increased [CnAn+1]? supramolecular aggregation. Consequently, highest yield of products obtained in ILs which show decreased anion-anion aggregation [A2 + H+]? abundance in ESI-MS. We anticipate our results to be a starting point for the establishment of desired ILs for organic synthesis.
Synthesis and Cytotoxicity of Diarylpentanoids against Sensitive CCRF-CEM and Multidrug-Resistant CEM/ADR5000 Leukemia Cells
Di Chio, Carla,Efferth, Thomas,Ettari, Roberta,Schirmeister, Tanja,Zhou, Min,Zappalà, Maria
, (2022/01/04)
This article described the synthesis and biological investigation of a series of symmetric diarylpentanoids, characterized by a dienone moiety and by a different pattern of substitution on the two phenyl rings. The series of compounds 1a–p were tested aga
Chalcones and bis-chalcones analogs as DPPH and ABTS radical scavengers
Bale, Adebayo Tajudeen,Salar, Uzma,Khan, Khalid Mohammed,Chigurupati, Sridevi,Fasina, Tolulope,Ali, Farman,Ali, Muhammad,Sekhar Nanda, Sitansu,Taha, Muhammad,Perveen, Shahnaz
, p. 249 - 257 (2021/04/21)
Background: A number of synthetic scaffolds, along with natural products, have been identified as potent antioxidants. The present study deals with the evaluation of varyingly substituted, medicinally distinct class of compounds “chalcones and bis-chalcon
Synthesis of tetracyclic oxindoles and evaluation of their α-glucosidase inhibitory and glucose consumption-promoting activity
Dodd, Robert H.,Hao, Lei,Ma, Ying,Ma, Yujiao,Sun, Hua,Yu, Peng,Zhang, Xinying,Zhang, Yinan,Zhao, Lianbo
supporting information, (2020/05/27)
A series of tetracyclic oxindole derivatives was synthesized by asymmetric 1, 3-dipole reaction in 2–4 steps in 57–86% overall yields. These compounds were evaluated for α-glucosidase inhibitory and glucose consumption-promoting activity in vitro. Compound 4l competitively and reversibly inhibited α-glucosidase (IC50 = 3.64 μM) with activity 14-fold higher than that of acarbose. Docking analysis substantiated these findings. In addition, compound 4l exhibited significant glucose consumption promoting activity at 1 μM.
Chalcones and bis-chalcones: As potential α-amylase inhibitors; synthesis, in vitro screening, and molecular modelling studies
Tajudeen Bale, Adebayo,Mohammed Khan, Khalid,Salar, Uzma,Chigurupati, Sridevi,Fasina, Tolulope,Ali, Farman,Kanwal,Wadood, Abdul,Taha, Muhammad,Sekhar Nanda, Sitanshu,Ghufran, Mehreen,Perveen, Shahnaz
, p. 179 - 189 (2018/05/24)
Despite of a diverse range of biological activities associated with chalcones and bis-chalcones, they are still neglected by the medicinal chemist for their possible α-amylase inhibitory activity. So, the current study is based on the evaluation of this c
Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin
Deck, Lorraine M.,Hunsaker, Lucy A.,Vander Jagt, Thomas A.,Whalen, Lisa J.,Royer, Robert E.,Vander Jagt, David L.
, p. 854 - 865 (2017/12/13)
Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. Nrf2 is widespread in the CNS and is recognized as an important regulator of brain inflammation. The natural product curcumin exhibits numerous biological activities including ability to induce the expression of Nrf2-dependent phase II and anti-oxidant enzymes. Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism. Enone analogues of curcumin were examined with an Nrf2 reporter assay to identify Nrf2 activators. Analogues were separated into groups with a 7-carbon dienone spacer, as found in curcumin; a 5-carbon enone spacer with and without a ring; and a 3-carbon enone spacer. Activators of Nrf2 were found in all three groups, many of which were more active than curcumin. Dose-response studies demonstrated that a range of substituents on the aromatic rings of these enones influenced not only the sensitivity to activation, reflected in EC50 values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2 by these analogues.
