22482-43-5Relevant articles and documents
Skeletally Tunable Seven-Membered-Ring Fused Pyrroles
Andreou, Dimitrios,Essien, Nsikak B.,Pubill-Ulldemolins, Cristina,Terzidis, Michael A.,Papadopoulos, Athanasios N.,Kostakis, George E.,Lykakis, Ioannis N.
supporting information, p. 6685 - 6690 (2021/09/11)
We describe a copper-mediated method that enables the synthesis of seven-membered-ring fused pyrroles (7-mrFPs). The protocol proceeds via an in situ spiro-intermediate ring expansion and tolerates a library of 7-mrFP derivatives with a broad range of functional groups in a simple step with tangible parameters and substrate adaptations. These rare 7-mrFPs are now accessible on a millimolar scale, and selected examples exhibit high antioxidant activity.
Exploiting the chiral ligands of bis(Imidazolinyl)-and bis(oxazolinyl)thiophenes—Synthesis and application in Cu-catalyzed friedel–crafts asymmetric alkylation
Al-Majid, Abdullah Mohammed,Alammari, Abdullah Saleh,Alshahrani, Saeed,Barakat, Assem,Haukka, Matti,Islam, Mohammad Shahidul
, (2021/12/17)
Five new C2-symmetric chiral ligands of 2,5-bis(imidazolinyl)thiophene (L1–L3) and 2,5-bis(oxazolinyl)thiophene (L4 and L5) were synthesized from thiophene-2,5-dicarboxylic acid (1) with enantiopure amino alcohols (4a–c) in excellent optical purity and chemical yield. The util-ity of these new chiral ligands for Friedel–Crafts asymmetric alkylation was explored. Subse-quently, the optimized tridentate ligand L5 and Cu(OTf)2 catalyst (15 mol%) in toluene for 48 h promoted Friedel–Crafts asymmetric alkylation in moderate to good yields (up to 76%) and with good enantioselectivity (up to 81% ee). The bis(oxazolinyl)thiophene ligands were more potent than bis(imidazolinyl)thiophene analogues for the asymmetric induction of the Friedel–Crafts asymmetric alkylation.
Compound containing FXR agonist, and preparation method and application thereof
-
Paragraph 0181-0184, (2020/03/25)
The invention belongs to the technical field of medicines, and concretely relates to a compound containing an FXR agonist, represented by general formula (I), or a pharmaceutically acceptable salt thereof, a preparation method of the compounds, a pharmaceutical composition and a pharmaceutical preparation containing the compounds, and an application of the compounds in the preparation of drugs used for treating and/or preventing FXR mediated diseases. R, R, R, R, m, n, p, q, T, L1-L2 and A ring or B ring in the formula (I) are defined in the description.
NHC-Catalyzed Dual Stetter Reaction: A Mild Cascade Annulation for the Syntheses of Naphthoquinones, Isoflavanones, and Sugar-Based Chiral Analogues
Mitra, Rajendra N.,Show, Krishanu,Barman, Debabrata,Sarkar, Satinath,Maiti, Dilip K.
, p. 42 - 52 (2019/01/10)
The N-heterocycle carbene (NHC)-catalyzed dual Stetter cascade reaction is discovered through coupling of β-nitrostyrene with phthalaldehyde under mild conditions to furnish valuable aryl-naphthoquinones. The generality of the new reaction is validated through the development of a C-C and O-C bond forming Stetter cascade reaction using salicylaldehydes to obtain functionalized dihydroisoflavanones. The mild NHC organocatalysis is successfully employed for the construction of optically pure sugar-based naphthoquinones and dihydroisoflavanones. Herein, NHC is found as a unique and powerful organocatalyst to construct homoatomic C-C cross-coupling, heteroatomic O-C bond formation, and cascade cyclization utilizing NO2 as a leaving group at ambient temperature. A mechanistic pathway of the new metal-free catalysis is predicted on the basis of our ESI-MS study of the ongoing reaction and literature.
Comprehensive evaluation of antioxidant effects of Japanese Kampo medicines led to identification of Tsudosan formulation as a potent antioxidant agent
Sato, Naoko,Li, Wei,Takemoto, Hiroaki,Takeuchi, Mio,Nakamura, Ai,Tokura, Emi,Akahane, Chie,Ueno, Kanako,Komatsu, Kana,Kuriyama, Noriko,Onoda, Toshihisa,Higai, Koji,Koike, Kazuo
, p. 163 - 172 (2018/11/06)
Oxidative stress due to the overproduction of reactive oxygen species plays an important role in the pathogenesis of various diseases. In the present study, we comprehensively evaluated the antioxidant activities of 147 oral formulations of Japanese traditional herbal medicines (Kampo medicines), representing the entire panel of oral Kampo medicines listed in the Japanese National Health Insurance Drug List, using in vitro radical scavenging assays, including the 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity assay, the superoxide anion scavenging activity assay, and the oxygen radical absorption capacity assay. Three of the formulations tested, namely, Tsudosan, Daisaikoto, and Masiningan, showed the most potent in vitro antioxidant activities and were selected for further investigation of their intracellular and in vivo antioxidant effects. The results of the 2′,7′-dichlorodihydrofluorescin diacetate assay demonstrated that all three Kampo medicines significantly inhibited hydrogen peroxide-induced oxidative stress in human hepatocellular liver carcinoma HepG2 cells. In addition, Tsudosan significantly increased the serum biological antioxidant potential values when orally administrated to mice, indicating that it also had in vivo antioxidant activity. The potent antioxidant activity of Tsudosan may be one of the mechanisms closely correlated to its clinical usage against blood stasis.
Design, synthesis and evaluation of thiourea derivatives as antimicrobial and antiviral agents
Ravichandran, Veerasamy,Shalini, Sivadasan,Kumar, Krishnan Suresh,Rajak, Harish,Agrawal, Ram Kishore
, p. 618 - 624 (2019/06/25)
Background: The development of drug-resistant by bacteria appears rapidly and thus making the effectiveness of antibiotics severely limited. Methods: A series of thiourea derivatives was synthesized, characterized and evaluated for their in vitro antibacterial, antifungal and antiviral activities. Results: Structures of the newly synthesized compounds were confirmed by elemental and spectral analysis. The biological results showed that some of the target compounds displayed comparable antimicrobial and antiviral activities with reference drugs. Structure-activity relationship studies revealed that the ortho-chloro or fluoro substituted phenyl at Ar1 and substituted pyridinyl at Ar2 positions of the thiourea nucleus are essential for their in vitro antimicrobial and anti-HIV activity. In particular, compounds 8 and 10 showed better activity against the tested bacteria, fungi and viral strains than other synthesized PET derivatives reported in the present study. Conclusion: These results provide an encouraging lead that could be used for the development of new potent antiviral and antimicrobial agents.
Synthesis of Benzo[4,5]imidazo[2,1-b]thiazole by Copper(II)-Catalyzed Thioamination of Nitroalkene with 1H-Benzo[d]imidazole-2-thiol
Jana, Sourav,Chakraborty, Amrita,Shirinian, Valerii Z.,Hajra, Alakananda
supporting information, p. 2402 - 2408 (2018/05/08)
A Copper(II)-catalyzed thioamination of β-nitroalkene with 1H-benzo[d]imidazole-2-thiol has been developed for the synthesis of benzo[4,5]imidazo[2,1-b]thiazole derivatives. A variety of N-fused benzoimidazothiazole derivatives are obtained in high yields through successive C?N and C?S bond formations. This protocol is also applicable to β-substituted β-nitroalkenes to afford 2,3-disubstituted benzoimidazothiazoles. (Figure presented.).
Synthesis of pyrimidine-2,4,6-trione derivatives: Anti-oxidant, anti-cancer, α-glucosidase, β-glucuronidase inhibition and their molecular docking studies
Barakat, Assem,Islam, Mohammad Shahidul,Al-Majid, Abdullah Mohammed,Ghabbour, Hazem A.,Yousuf, Sammer,Ashraf, Mahwish,Shaikh, Nimra Naveed,Iqbal Choudhary,Khalil, Ruqaiya,Ul-Haq, Zaheer
supporting information, p. 72 - 79 (2016/07/26)
This paper describes a facile protocol, efficient, and environmentally benign for the synthesis a series of barbiturate acid substituted at C5 position 3a–o. The desired compounds subjected in vitro for different set of bioassays including against anti-oxidant (DPPH and super oxide scavenger assays), anti-cancer, α-glucosidase and β-glucuronidase inhibitions. Compound 3m (IC50?=?22.9?±?0.5?μM) found to be potent α-glucosidase enzyme inhibitors and showed more activity than standard acarbose (IC50?=?841?±?1.73?μM). Compound 3f (IC50?=?86.9?±?4.33?μM) found to be moderate β-Glucuronidase enzyme inhibitors and showed activity comparatively less than the standard D-saccharic acid 1,4-lactone (IC50?=?45.75?±?2.16?μM). Furthermore, in sillico investigation was carried out to investigate bonding mode of barbiturate acid derivatives.
