7400-08-0Relevant articles and documents
Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites
Ali, Wajid,Anjana, S. S.,Bhattacharya, Trisha,Chandrashekar, Hediyala B.,Goswami, Nupur,Guin, Srimanta,Maiti, Debabrata,Panda, Sanjib,Prakash, Gaurav,Saha, Argha,Sasmal, Sheuli,Sinha, Soumya Kumar
, p. 1929 - 1940 (2022/02/01)
The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had
Reusable, magnetic Raney nickel based palladium catalysts for the Heck coupling in aqueous media
Bumagin, N. A.
, p. 2034 - 2040 (2021/11/05)
Hybrid materials based on Pd- and Cu-doped Raney nickel appeared to be highly efficient catalysts for the Heck reaction in aqueous media in the absence of organic cosolvents. The catalysts can be easily removed by an external magnet and reused without losing catalytic activity.
Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation
Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei
supporting information, p. 5905 - 5908 (2021/06/18)
A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.
Novel ester derivative of cinnamates with different long alkoxy chain: synthesis, mesomorphic properties, biological evaluation
Bhalodiya, Pradip C.,Patel, Hemant N.,Parmar, Tejasvi H.,Sangani, Chetan B.,Rajani, Dhanji P.
, p. 1 - 25 (2021/07/07)
A novel series of liquid crystals involving cinnamate-based mesogenic units interlinked between aromatic ester and alkyl bromide were designed and synthesized. All target molecules were confirmed by IR, 1H NMR, 13C NMR, ESI-MS, and elemental analysis. The mesomorphic behavior of novel synthesized materials (P1–P18), (V1–V18), and (M1–M18) was investigated through a polarizing optical microscope, differential scanning calorimetry, and thermogravimetric analysis (TGA) analysis. The lower carbon chain substituted member showed nematic phase while compound possess higher carbon chain exhibited only SmC phase. Thermal stability is determined by TGA analysis. All the cinnamate derivatives were screened for their anti-microbial, anti-malarial, and anti-tuberculosis potency. Among them, most of the derivatives exhibited outstanding anti-bacterial and anti-tuberculosis activity. Some derivatives also exhibited potent anti-fungal activity.
Acylated pelargonidin and cyanidin 3-sambubiosides from the flowers of Aeschynanthus species and cultivars
Iwashina, Tsukasa,Mizuno, Takayuki,Rahayu, Sri,Sugahara, Kohtaro,Tsutsumi, Chie,Widyatmoko, Didik
, (2021/10/01)
Thirteen anthocyanins were isolated from the flowers of two Aeschynanthus species, A. fulgens and A. pulcher, and six cultivars, ‘Mahligai’, ‘Mona Lisa’, ‘SoeKa’, ‘Redona’, ‘Freshya’ and ‘Bravera’, and identified as pelargonidin and cyanidin 3-O-sambubiosides and their malonates, succinates, p-coumarates and caffeates, and pelargonidin 3-O-glucoside by acid hydrolysis, HR-MS and NMR. Of their anthocyanins, pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-malonylglucoside)] (2), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-succinylglucoside)] (3), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-E-p-coumaroylglucoside)] (4), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-Z-p-coumaroylglucoside)] (5), pelargonidin 3-O-[xylosyl-(1 → 2)-(6''-E-caffeoylglucoside)] (6) and cyanidin 3-O-[xylosyl-(1 → 2)-(6''-succinylglucoside)] (9) were reported in nature for the first time.
Design, synthesis, and evaluation of different scaffold derivatives against NS2B-NS3 protease of dengue virus
Ganji, Lata R.,Gandhi, Lekha,Musturi, Venkataramana,Kanyalkar, Meena A.
, p. 285 - 301 (2020/11/19)
The number of deaths or critical health issues is a threat in the infection caused by Dengue virus, which complicates the situation, as only symptomatic treatment is the current solution. In this regard we have targeted the dengue protease NS2B-NS3 that is responsible for the replication. The series was designed with the help of molecular modeling approach using docking protocols. The series comprised of different scaffolds viz. cinnamic acid analogs (CA1–CA11), chalcone (C1–C10) and their molecular hybrids (Lik1–Lik10), analogs of benzimidazole (BZ1-BZ5), mercaptobenzimidazole (BS1-BS4), and phenylsulfanylmethylbenzimidazole (PS1-PS4). Virtual screening of various natural phytoconstituents was employed to determine the interactions of designed analogs with the residues of catalytic triad in the active site of NS2B-NS3. We have further synthesized the selected leads. The synthesized analogs were evaluated for the cytotoxicity and NS2B-NS3 protease inhibition activity and compared with known anti-dengue natural phytoconstituent quercetin as the standard. CA2, BZ1, and BS2 were found to be more potent and efficacious than the standard quercetin as evident from the protease inhibition assay.
Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters
Gao, Ang,Jiang, Run-Chuang,Liu, Chuang-Chuang,Liu, Qi-Le,Lu, Xiao-Yu,Xia, Ze-Jie
supporting information, p. 8829 - 8842 (2021/06/30)
Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.
Ballodiolic acid a and b: Two new ros, (? oh), (onoo? ) scavenging and potent antimicrobial constituents isolated from ballota pseudodictamnus (l.) benth.
Ahmad, Ijaz,Ahmad, Nisar,Alobaid, Abdulrahman,Amin, Syed Badar,Bari, Ahmed,Fozia,Mahmood, Hafiz Majid,Shaheen, Asmat,Sohaib, Muhammad,Ullah, Riaz
, (2021/04/07)
Bioassays guided phytochemical investigations on the ethyl acetate-soluble fraction of the root material of Ballota pseudodictamnus (L.) Benth. led to the isolation of two new compounds, ballodiolic acid A (1) and ballodiolic acid B (2), along with three known compounds ballodiolic acid (3), ballotenic acid (4), and β-amyrin (5), which were also isolated for the first time from this species by using multiple chromatographic techniques. The structures of the compounds (1–5) were determined by modern spectroscopic analysis including 1D and 2D NMR techniques and chemical studies. In three separate experiments, the isolated compounds (1–5) demonstrated potent antioxidant scavenging activity, with IC50 values ranging from 07.22–34.10 μM in the hydroxyl radical (? OH) inhibitory activity test, 58.10–148.55 μM in the total ROS (reactive oxygen species) inhibitory activity test, and 6.23–69.01 μM in the peroxynitrite (ONOO? ) scavenging activity test. With IC50 values of (07.22 ± 0.03, 58.10 ± 0.07, 6.23 ± 0.04 μM) for? OH, total ROS, and scavenge ONOO?, respectively, ballodiolic acid B (2) showed the highest scavenging ability. Antibacterial and antifungal behaviors were also exposed to the pure compounds 1–5. In contrast to compounds 4 and 5, compounds 1–3 were active against all bacterial strains studied, with a good zone of inhibition proving these as a potent antibacterial agent. Similarly, compared to compounds 3–5, compounds 1 and 2 with a 47 percent and 45 percent respective inhibition zone were found to be more active against tested fungal strains.
Amino Group Functionalized Hf-Based Metal-Organic Framework for Knoevenagel-Doebner Condensation
Das, Aniruddha,Anbu, Nagaraj,Gogoi, Chiranjib,Dhakshinamoorthy, Amarajothi,Biswas, Shyam
, p. 3396 - 3403 (2021/08/20)
A Hf(IV) metal-organic framework (MOF) with di-amino functionalized linker was obtained as a crystalline solid with UiO-67 topology under solvothermal reaction conditions. The guest free form of Hf(IV) MOF (1′) was efficiently employed as a heterogeneous catalyst to synthesize cinnamic acid derivatives via Knoevenagel-Doebner reaction for the first time. The catalyst (1′) was efficiently active to directly achieve cinnamic acid from benzaldehyde and malonic acid. The solid retained its activity up to 6th cycle with no decay in its activity. The noticeable advantages of the catalyst are its milder reaction conditions, high yield, high stability, recyclable nature towards catalysis and wide substrate scope as well as shape-selective behaviour. The possible mechanism of the reaction was also studied thoroughly with suitable control experiments.
Identification of novel functionalized carbohydrazonamides designed as chagas disease drug candidates
Do Nascimento, Mayara S. S.,Camara, Vitória R. F.,da Costa, Juliana S.,Barbosa, Juliana M. C.,Lins, Alessandra S. M.,Salom?o, Kelly,de Castro, Solange L.,Carvalho, Samir A.,da Silva, Edson F.,Fraga, Carlos A. M.
, p. 774 - 783 (2020/08/19)
Background: Although several research efforts have been made worldwide to discover novel drug candidates for the treatment of Chagas disease, the nitroimidazole drug benznidazol remains the only therapeutic alternative in the control of this disease. However, this drug presents reduced efficacy in the chronic form of the disease and limited safety after long periods of admini-stration, making it necessary to search for new, more potent and safe prototypes. Objective: We described herein the synthesis and the trypanocidalaction of new functionalized carbohydrazonamides (2-10) against trypomastigote forms of Trypanosoma cruzi. Methods: These compounds were designed through the application of molecular hybridization concept between two potent anti-T. cruzi prototypes, the nitroimidazole derivative megazol (1) and the cinnamyl N-acylhydrazone derivative (14) which have been shown to be twice as potent in vitro as benznidazole. Results: The most active compounds were the (Z)-N'-((E)-3-(4-nitrophenyl)-acryloyl)-1-methyl-5-nitro-1H-imidazol-2-carbohydrazonamide (6) (IC50 =9.50 μM) and the (Z)-N'-((E)-3-(4-hydroxyphe-nyl)-acryloyl)-1-methyl-5-nitro-1H-imidazol-2-carbohydrazonamide (8) (IC50 =12.85 μM), which were almost equipotent to benznidazole (IC50 =10.26 μM) used as standard drug. The removal of the amine group attached to the imine subunit in the corresponding N-acylhydrazone derivatives (11-13) resulted in less potent or inactive compounds. The para-hydroxyphenyl derivative (8) presented also a good selectivity index (SI = 32.94) when tested against mammalian cells from Swiss mice. Conclusion: The promising trypanocidal profile of new carbohydrazonamide derivatives (6) and (8) was characterized. These compounds have proved to be a good starting point for the design of more effective trypanocidal drug candidates.
