Synthesis of the 1,5-disubstituted tetrazole-methanesulfonylindole hybrid system via high-order multicomponent reaction

• Cesia M. Aguilar-Morales,
• América A. Frías-López,
• Nadia V. Emilio-Velázquez,
• Alejandro Islas-Jácome,
• Angelica Judith Granados-López,
• Jorge Gustavo Araujo-Huitrado,
• Yamilé López-Hernández,
• Hiram Hernández-López,
• Luis Chacón-García,
• Jesús Adrián López and
• Carlos J. Cortés-García

Beilstein J. Org. Chem. 2024, 20, 3077–3084, doi:10.3762/bjoc.20.256

• highly bioactive compounds that can be converted into drug candidates in a fast and efficient manner containing these moieties is the molecular hybridization [8][9][10]. It consists of covalently joining of two or more pharmacophoric fragments to provide new hybrid compounds with improved efficacy and

• previously described strategies involved the use of higher-order multicomponent reactions (HO-MCRs). As part of our ongoing research program towards the synthesis of novel hybrid compounds based on the 1,5-disubstituted tetrazole moiety [23][24][25][26][27], we developed a synthetic strategy for the

• bioactivity study was proposed based on observations that indole-coumarin-thiadiazole hybrid compounds described by Kamath et al. [44], as well as indole-benzimidazole hybrids reported by Singla et al. [45] have shown potential as therapeutic agents for breast cancer treatment. Thereby, we hypothesized that

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

• Cristina Martini,
• Muhammad Idham Darussalam Mardjan and
• Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

Recent developments in the engineered biosynthesis of fungal meroterpenoids

• Zhiyang Quan and
• Takayoshi Awakawa

Beilstein J. Org. Chem. 2024, 20, 578–588, doi:10.3762/bjoc.20.50

• Zhiyang Quan Takayoshi Awakawa RIKEN Center for Sustainable Resource Science, Wako, Saitama 351-0198, Japan 10.3762/bjoc.20.50 Abstract Meroterpenoids are hybrid compounds that are partially derived from terpenoids. This group of natural products displays large structural diversity, and many

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

• Dmitry B. Vinogradov,
• Alexei N. Izmest’ev,
• Angelina N. Kravchenko,
• Yuri A. Strelenko and
• Galina A. Gazieva

Beilstein J. Org. Chem. 2023, 19, 1047–1054, doi:10.3762/bjoc.19.80

• closely related hybrid compounds including fragments of 1,3-thiazine and imidazo-1,2,4-triazine is still highly relevant. Earlier we have demonstrated that imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazines and their derivatives functionalized at position 6 are capable of undergoing skeletal rearrangements and

Cholyl 1,3,4-oxadiazole hybrid compounds: design, synthesis and antimicrobial assessment

• Anas J. Rasras,
• Mohamed El-Naggar,
• Nesreen A. Safwat and
• Raed A. Al-Qawasmeh

Beilstein J. Org. Chem. 2022, 18, 631–638, doi:10.3762/bjoc.18.63

The use of isoxazoline and isoxazole scaffolding in the design of novel thiourea and amide liquid-crystalline compounds

• Itamar L. Gonçalves,
• Rafaela R. da Rosa,
• Vera L. Eifler-Lima and
• Aloir A. Merlo

Beilstein J. Org. Chem. 2020, 16, 175–184, doi:10.3762/bjoc.16.20

• previously published [19][21][22][23][24]. The synthetic route used for the synthesis of the hybrid compounds, N-acyl-N'-isoxazolinylthioureas 17a–c and N-acyl-N'- isoxazolylthioureas 18a–c is outlined in Scheme 2. The synthesis of thioureas 17a–c and 18a–c involved the activation of 4-heptyloxybenzoic acid

Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

• Gerardo M. Ojeda,
• Prabhat Ranjan,
• Pavel Fedoseev,
• Lisandra Amable,
• Upendra K. Sharma,
• Daniel G. Rivera and
• Erik V. Van der Eycken

Beilstein J. Org. Chem. 2019, 15, 2447–2457, doi:10.3762/bjoc.15.237

• could form isoquinolones and pyridones linked to a tetrazole ring, since such class of hybrid compounds is not described in the literature. Several protocols based on C–H activation or metal-catalyzed cyclizations are known to generate the isoquinolone and pyridone moieties and further assist their post

• explored with substrates bearing acyl groups other than benzoyl (Scheme 5). Compounds incorporating acrylamidomethyltetrazole fragments reacted with diphenylacetylene to form the tetrazole/pyridone hybrids 5a–c in good yields. In addition, very complex hybrid compounds based on heterocyclic, fused aromatic

• reactions (MCRs) with the large synthetic scope of metal-catalyzed cyclization protocols [49][50][51][52][53][54]. In this sense, we envisioned that the application of modern Ru(II) or Rh(III)-catalyzed annulations on Ugi-azide-4CR-derived scaffolds could be a promising strategy to generate novel hybrid

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• the preparation of steroidal derivatives with a pyrimidine moiety fused to ring D. This heterocycle moiety appears in different biologically active steroids fused to ring D, and previous non-MCR methods had been reported for the creation of libraries of such hybrid compounds [40]. The Biginelli

Synthesis of 3-aminocoumarin-N-benzylpyridinium conjugates with nanomolar inhibitory activity against acetylcholinesterase

• Nisachon Khunnawutmanotham,
• Cherdchai Laongthipparos,
• Patchreenart Saparpakorn,
• Nitirat Chimnoi and
• Supanna Techasakul

Beilstein J. Org. Chem. 2018, 14, 2545–2552, doi:10.3762/bjoc.14.231

• . Hybrid compounds such as huperzine A–tacrine hybrids [5], donepezil–tacrine hybrid related derivatives [6][7] and tacrine–indole hybrids [8] with dual-binding site properties exhibit potent AChE inhibition activities. In addition, coumarin compounds linked with various side chain moieties [9][10][11] as

Synthesis and spectroscopic properties of β-meso directly linked porphyrin–corrole hybrid compounds

• Baris Temelli and
• Hilal Kalkan

Beilstein J. Org. Chem. 2018, 14, 187–193, doi:10.3762/bjoc.14.13

• -5,10,15,20-tetraphenylporphyrins with meso-substituted dipyrromethanes. Hybrid compounds have been characterized by 1H NMR, 13C NMR, 2D NMR, UV–vis absorption and fluorescence spectroscopy. Keywords: corrole; hybrid compounds; indium(III) chloride; porphyrin; porphyrinoids; Introduction Porphyrins and

• intramolecular energy transfer between macrocycles [38]. As a part of our ongoing research on porphyrin–corrole conjugates, herein we describe a convenient synthesis of a series of novel directly linked porphyrin–corrole hybrid compounds. For this purpose, acid-catalyzed reactions of dipyrromethanes and

• with aldehydes [42]. When electron-withdrawing 4-nitrophenyl and pentafluorophenyl substituents were used on the dipyrromethane, hybrid compounds 4c and 4e were isolated in 16% and 20% yields, respectively. The synthesis of 4e with InCl3 afforded a very low yield, thus an equimolar amount of AlCl3 was

Dicarboxylic esters: Useful tools for the biocatalyzed synthesis of hybrid compounds and polymers

• Ivan Bassanini,
• Karl Hult and
• Sergio Riva

Beilstein J. Org. Chem. 2015, 11, 1583–1595, doi:10.3762/bjoc.11.174

• different bioactive molecules with suitable dicarboxylic acids to prepare hybrid compounds has been receiving more and more attention. The interest is due to the fact that these new substances might show additive activities [36], having improved properties or efficacies compared to the combined use of the

• once again the well-known efficiency, selectivity and versatility of CAL-B (Novozyme 435) [16]. As in the previous examples, the mixed esters from the first esterification step can be used as acylating agents in the second esterification step. Scheme 3 shows the synthesis of the hybrid compounds 17 and

Multicomponent reactions in nucleoside chemistry

• Mariola Koszytkowska-Stawińska and
• Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

• moderate yields. Antiparasitic activities of the hybrid compounds 15 were evaluated; some of them showed moderate activities against trypomastigote forms of Trypanosoma brucei brucei GVR 35 (e.g., IC50 = 25 µM for Ar = C6H4-Cl-4). The Mannich reaction was also used to construct nucleoside scaffolds from

• . Activity of hybrid compounds 28 and 29 against VZV and CMV viruses, as well as against Leishmania donovani promastigotes, was evaluated. Unfortunately, none of them showed any activity up to 250 μM. 3. The Ugi reaction The Ugi reaction allows for a facile synthesis of a bisamide from a ketone (or an

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

• Alexander O. Terent'ev,
• Dmitry A. Borisov,
• Vera A. Vil’ and
• Valery M. Dembitsky

Beilstein J. Org. Chem. 2014, 10, 34–114, doi:10.3762/bjoc.10.6

Synthesis of meso-substituted dihydro-1,3-oxazinoporphyrins

• Satyasheel Sharma and
• Mahendra Nath

Beilstein J. Org. Chem. 2013, 9, 496–502, doi:10.3762/bjoc.9.53

• anticancer significance of these two classes of molecules, it was contemplated to construct new dihydro-1,3-oxazinoporphyrins combining the porphyrin and dihydro-1,3-oxazine moieties in a single molecular framework. Such hybrid compounds may prove useful for pharmacological studies or in the development of