Figure - uploaded by Khurshed Bozorov
Content may be subject to copyright.
Source publication
![ipso-Nitration of p-tert-butylcalix[n]arenes using different nitrating...](profile/Khurshed-Bozorov/publication/346921811/figure/tbl1/AS:968469235388417@1607912467682/ipso-Nitration-of-p-tert-butylcalixnarenes-using-different-nitrating-reagents_Q320.jpg)
Context in source publication
Context 1
... (II) acetate was selected for the condition screening with AgNO3 as a nitrating agent, and water as the solvent. The results indicated that 60 mol% Cu(OAc) 2 converted the substrate into a nitro product at 92% yield (Table 4). When NaNO 3 and La(NO 3 ) 3 were each used as the nitrating agent, the nitro products were formed at yields of 72 and 66%, respectively. ...Citations
... The tricyclic deoxyvasicinone system is part of other biologically important alkaloids including isaindigotone [27], tryptanthrin [28], and luotonin A [29], while mackinazolinone is part of rutaecarpine [30] and evodiamine [31], respectively (Fig. 1). Our research group performed large studies on the synthetic analogs of deoxyvasicinone and mackinazolinone, which containing carbonyl (C=O) group in the pyrimidine ring [32][33][34][35][36][37][38]. Results revealed that several modified analogs of these alkaloids exhibited satisfactory higher antiproliferative activity against a panel of human cancer cell lines [32,39]. ...
Herein, we studied the formation of thiones via C=O group conversion into the C=S functional group-based tricyclic pyrimidinone systems using Lawesson’s reagent and phosphorus pentasulfide as thionation agents. Naturally occurring alkaloids deoxyvasicinone and mackinazolinone were selected as templates for the modification of furo[2,3-d]pyrimidinone and pyrrolo[2,3-d]pyrimidinone scaffold. Research work was performed under the combinatorial and parallel synthesis of pyrimidine-based small molecules, along with a one-pot reaction strategy. All synthesized 54 novel pyrimidine-thiones were elucidated by ¹H-NMR, ¹³C-NMR, and HRMS analysis. In addition, both series of thiones were evaluated for their antitumor activity against three types of the human cancer cell: cervical HeLa, breast MCF-7, and colon HT-29 lines. Compound with azepine fragment 13aa (1-methyl-2-(4-(trifluoromethyl)phenyl)-1,6,7,8,9,10-hexahydro-4H-pyrrolo[2’,3’:4,5]pyrimido[1,2-a]azepine-4-thione) was most active derivative (IC50 = 2.09 ± 0.22 µM) against the HT-29 cell line.
Graphical abstract
... Electrophilic nitration of substituted aromatics has low regioselectivity, due to the formation of various isomers, while nitration through direct oxidation of amine and azide produces by-products (hydroxylamine, nitroso, nitro, oxime, azo, azoxy), as well as restricts the number of suitable oxidizing reagents that can be used to produce efficient conversions. Ipso-nitration involves the nucleophilic conversion of functional groups into nitro groups (Scheme 12) [42]. ...
Infectious diseases commonly occur in tropical and sub-tropical countries. The pathogens of such diseases are able to multiply in human hosts, warranting their continual survival. Infections that are commonplace include malaria, chagas, trypanosomiasis, giardiasis, amoebiasis, toxoplasmosis and leishmaniasis. Malaria is known to cause symptoms, such as high fever, chills, nausea and vomiting, whereas chagas disease causes enlarged lymph glands, muscle pain, swelling and chest pain. People suffering from African trypanosomiasis may experience severe headaches, irritability, extreme fatigue and swollen lymph nodes. As an infectious disease progresses, the human host may also experience personality changes and neurologic problems. If left untreated, most of these diseases can lead to death.
Parasites, microbes and bacteria are increasingly adapting and generating strains that are resistant to current clinical drugs. Drug resistance creates an urgency for the development of new drugs to treat these infections. Nitro containing drugs, such as chloramphenicol, metronidazole, tinidazole and secnidazole had been banned for use as antiparasitic agents due to their toxicity. However, recent discoveries of nitrocontaining anti-tuberculosis drugs, i.e. delamanid and pretonamid, and the repurposing of flexinidazole for use in combination with eflornithine for the treatment of human trypanosomiasis, have ignited interest in nitroaromatic scaffolds as viable sources of potential anti-infective agents.
This review highlights the differences between old and new nitration methodologies. It furthermore offers insights into recent advances in the development of nitroaromatics as anti-infective drugs.
... Ipso additions/substitutions typically occur under specialized circumstances, such as certain nitration reactions [41] Fig. 6. Frequency of chlorine addition/substitution in the N eq FMD simulation over the 29 atoms comprising OxBZ. ...
Gas-phase reactions of ozone (O3) with volatile organic compounds were investigated both by experiment and molecular simulations. From our experiments, it was found ozone readily reacts with VOC pure components and reduces it effectively. By introducing ozone intermittently, the reaction between VOC and ozone is markedly enhanced. In order to understand the relationship between intermediate reactions and end products, ozone reaction with benzene and alicyclic monoterpene sabinene were simulated via a novel hybrid quantum mechanical/molecular mechanics (QM/MM) algorithm that forced repeated bimolecular collisions. Molecular orbital (MO) rearrangements (manifested as bond dissociation or formation), resulting from the collisions, were computed by semi-empirical unrestricted Hartree-Fock methods (e.g., RM1). A minimum of 975 collisions between ozone and targeted organic species were performed to generate a distribution of reaction products. Results indicated that benzene and sabinene reacted with ozone to produce a range of stable products and intermediates, including carbocations, ring-scission products, as well as peroxy (HO2 and HO3) and hydroxyl (OH) radicals. Among the stable sabinene products observed included formaldehyde and sabina-ketone, which have been experimentally demonstrated in gas-phase ozonation reactions. Among the benzene ozonation products detected composed of oxygen mono-substituted aromatic C6H5O, which may undergo further transformation or rearrangement to phenol, benzene oxide or 2,4-cyclohexadienone; a phenomenon which has been experimentally observed in vapor-phase photocatalytic ozonation reactions.
Kimyoviy terapiyada o’sma hujayralarga qarshi tanlab ta’sir qiladigan moddalar ichida azot saqlagan geterosiklik birikmalar – triazollar muhim sinf birikmalari hisoblanadi. Mazkur sharhli maqolada 2022 yilda saraton hujayralariga qarshi yuqori faollik namoyon qilgan triazol-gibrid birikmalarning biologik faolliklari va bunday faollikga sabab bo’lgan ba’zi farmakofor guruhlar muhokama qilingan.
We report the synthesis, molecular docking and anticancer properties of the novel compound (E)-1-methyl-9-(3-methylbenzylidene)-6,7,8,9-tetrahydropyrazolo[3,4-d]pyrido[1,2-a]pyrimidin-4(1H)-one (PP562). PP562 was screened against sixteen human cancer cell lines and exhibited excellent antiproliferative activity with IC50 values ranging from 0.016 to 5.667 μM. Experiments were carried out using the target PP562 at a single dose of 1.0 μM against a kinase panel comprising 100 different enzymes. A plausible binding mechanism for PP562 inhibition of DDR2 was determined using molecular dynamic analysis. The effect of PP562 on cell proliferation was also examined in cancer cell models with both high and low expression of the DDR2 gene; PP562 inhibition of high-expressing cells was more prominent than that for low expressing cells. PP562 also exhibits excellent anticancer potency toward the HGC-27 gastric cancer cell line. In addition, PP562 inhibits colony formation, cell migration, and adhesion, induces cell cycle arrest at the G2/M phase, and affects ROS generation and cell apoptosis. After DDR2 gene knockdown, the antitumor effects of PP562 on tumor cells were significantly impaired. These results suggested that PP562 might exert its inhibitory effect on HCG-27 proliferation through the DDR2 target.
The chemical transformation of the tricyclic furo[2,3-d]pyrimidines was performed under isosteric and scaffold-hopping strategies focusing on the synthesis of its arylidene and imine-containing derivatives. Naturally-occurring alkaloids mackinazolinone and isaindigotone were as templates of target heterocycles. Synthesized compounds evaluated for their antitumor activity on human cancer cervical HeLa, breast MCF-7, and colon HT-29 cell lines. Four compounds: 8c, 8e, 10b, and 10c demonstrated potency against HeLa and HT-29 cell lines, and IC50 values were between 7.37-13.72 µM, respectively. The molecular docking results showed that compounds 8c and 10b had good binding and high matching with the target EGFR protein.
Xinazolin alkaloidlari xalq tabobatida qo’llaniladigan o’simliklar tarkibida keng uchraydi. So’nggi yillarda, farmakologiyada xinazolin alkaloidlarining tiofenli analoglari istiqbolli sinf birikmalari sifatida e’tirof etilmoqda. Mazkur sharhli maqola xinazolin alkaloidlarining tiofenli analoglari, jumladan 2-alkil- va aril tiyeno[2,3-d]pirimidinonlar sintezi va ularning transformasiyasiga bag’ishlangan.
A new selective nitration methodology is reported in which MOFs/sodium nitrite is used. A wide range of compounds such as boronic acids, aryl halides, aryl trifluoromethanesulfonate and aroyl chlorides were nitrated in the presence of a catalytic amount of palladium (Pd) embedded into MIL-101(Cr)-NH2 as a porous metal-organic frameworks (MOFs). The described method provides a beneficial and convenient strategy for chemo and homoselective ipso-nitration reaction. In contrast to the previously reported methodologies, acid nitric (HNO3) was not used in the course of the nitration reaction. The presented method was applied for the ipso-nitration of a broad range of compounds (47 samples) under mild conditions.
Nitro compounds are a predominant class of synthetic intermediates and building blocks for the preparation of a wide range of nitrogen-containing compounds in the chemical industry. As such, impressive progress has been currently made in the nitration of aromatics and olefins with excellent functional group tolerance and site-selectivity. In this mini review, we intend to highlight the regiospecific nitration of arenes and alkenes in various reaction systems. The involved mechanisms are discussed as well.
Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.
