Microwave-assisted synthesis of biologically relevant steroidal 17-exo-pyrazol-5'-ones from a norpregnene precursor by a side-chain elongation/heterocyclization sequence

• Gergő Mótyán,
• László Mérai,
• Márton Attila Kiss,
• Zsuzsanna Schelz,
• Izabella Sinka,
• István Zupkó and
• Éva Frank

Beilstein J. Org. Chem. 2018, 14, 2589–2596, doi:10.3762/bjoc.14.236

• . This indicates that the pyrazolone heterocyclic ring at the 17β position is a promising scaffold for the design of anticancer agents of the Δ5 androstene series. 1H NMR spectra of compound 7f in CDCl3 (top; # solvent signal) and in DMSO-d6 (bottom; # solvent signal). Multistep synthesis of steroidal β

Natural and redesigned wasp venom peptides with selective antitumoral activity

• Marcelo D. T. Torres,
• Gislaine P. Andrade,
• Roseli H. Sato,
• Cibele N. Pedron,
• Tania M. Manieri,
• Giselle Cerchiaro,
• Anderson O. Ribeiro,
• Cesar de la Fuente-Nunez and
• Vani X. Oliveira Jr.

Beilstein J. Org. Chem. 2018, 14, 1693–1703, doi:10.3762/bjoc.14.144

• eventual clinical development, as it displayed reduced hemolytic activity than Dec-NH2 and exhibited selective killing of cancer cells. The ACPs described here represent excellent scaffolds for the generation of potent, non-toxic, and selective anticancer agents. Experimental Peptide synthesis

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

• cancer cells towards apoptosis through the mitochondrial pathway. Mitrasinovic has reported sequence-dependent binding of various structurally different flavonoids (quercetin (QUE) and flavopiridol (FLP)), a family of prospective anticancer agents, to duplex DNAs [104]. The five hydroxy groups in QUE

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

• Eirinaios I. Vrettos,
• Gábor Mező and
• Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

• diminishing expressed nucleoside receptors responsible for the cell uptake of gemcitabine [6]. Additionally, chemotherapy with anticancer agents is often hampered by their poor aqueous solubility, low oral bioavailability and metabolic instability. These drawbacks are linked to the unfavorable ADME

• original anticancer agents is their uncontrolled toxicity which results in severe side effects. Without the addition of a targeting moiety, they bear low capacity to discriminate cancerous from normal cells. Moreover, the addition of a peptide as a targeting vehicle can enhance the pharmacokinetic and

• most common anticancer agents used against a wide variety of tumors. It is sold under the brand name Taxol by Bristol-Myers Squibb Company and is FDA approved for the treatment of breast cancer, ovarian cancer, non-small cell lung cancer and AIDS-related Kaposi's sarcoma. The main disadvantages in the

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

• Ranjana Aggarwal and
• Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

• [3,4-d]pyrimidine derivatives 221 (Scheme 59). The synthesized pyrazolo[3,4-d]pyrimidines 221 were proved to be good anticancer agents by MTT assay against HL-60 cancer cell lines. Zhang et al. [135] reported the reaction of 5-amino-4-cyanopyrazole 208 and aliphatic acids (R2COOH) in the presence of

Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines)

• Michał Nowacki and
• Krzysztof Wojciechowski

Beilstein J. Org. Chem. 2018, 14, 194–202, doi:10.3762/bjoc.14.14

• as anticancer agents [1][6][7] (Figure 1). Synthetic strategies towards indolo[3,2-b]quinolines have been reviewed [8]. These methodologies usually employ multistep procedures. Selected starting materials applicable to the synthesis of indolo[3,2-b]quinolines are presented in Scheme 1. Bis(2

Total syntheses of the archazolids: an emerging class of novel anticancer drugs

• Stephan Scheeff and
• Dirk Menche

Beilstein J. Org. Chem. 2017, 13, 1085–1098, doi:10.3762/bjoc.13.108

• the archazolids, complex polyketide macrolides which present the most potent V-ATPase inhibitors known to date, rendering these macrolides important lead structures for the development of novel anticancer agents. The limited natural supply of these metabolites from their myxobacterial source renders

• become important lead structures for the development of novel anticancer agents. As shown in Scheme 1 for the most prominent representatives archazolid A (1) and B (2) [38][39][40], their unique architectures are characterized by a 24-membered macrolactone ring with seven alkenes, including a

• a more concise route may be possible. Efforts are now being directed in the design and development of truly practicable and scalable routes to more stable archazolids to enhance the further preclinical development of these novel anticancer agents. Particular importance will be the development of a

First DMAP-mediated direct conversion of Morita–Baylis–Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates

• Marwa Ayadi,
• Haitham Elleuch,
• Emmanuel Vrancken and
• Farhat Rezgui

Beilstein J. Org. Chem. 2016, 12, 2906–2915, doi:10.3762/bjoc.12.290

• ] since they are considered as important surrogates for α-amino carboxylic acids, peptide mimics as well as versatile intermediates for the design of potential anticancer agents. β-Aminophosphonates present also an important place among the various compounds containing both a P–C bond and an amino group

Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates

• Jarosław Lewkowski,
• Maria Rodriguez Moya,
• Anna Wrona-Piotrowicz,
• Janusz Zakrzewski,
• Renata Kontek and
• Gabriela Gajek

Beilstein J. Org. Chem. 2016, 12, 1229–1235, doi:10.3762/bjoc.12.117

• was observed for N-benzyl substitution (3Aa). Results obtained for the α-hydroxyphosphonate 5A (IC50 = 25.8 µM against HT29) give the impact to look for potential anticancer agents among the α-hydroxyphosphonic derivatives. Conclusion A large series of various amino(pyren-1-yl)methylphosphonates was

Indenopyrans – synthesis and photoluminescence properties

• Andreea Petronela Diac,
• Ana-Maria Ţepeş,
• Albert Soran,
• Ion Grosu,
• Anamaria Terec,
• Jean Roncali and
• Elena Bogdan

Beilstein J. Org. Chem. 2016, 12, 825–834, doi:10.3762/bjoc.12.81

• ]isochromen-5(11H)-ones have been reported as key intermediates for the development of several topoisomerase I (Top1) anticancer agents [4][5][6][7]. A natural product exhibiting very promising antitumor activity is β-lapachone having a naphtho[1,2-b]pyrandione skeleton [8][9]. Also worth mentioning in this

Synthesis of Xenia diterpenoids and related metabolites isolated from marine organisms

• Tatjana Huber,
• Lara Weisheit and
• Thomas Magauer

Beilstein J. Org. Chem. 2015, 11, 2521–2539, doi:10.3762/bjoc.11.273

• therefore of great interest for drug discovery, especially for their application as anticancer agents [1]. Marine soft corals of the genus Xenia (order Alcyonacea, family Xeniidae) are known to be rich in xenicane diterpenoids. The first reported member of these metabolites was xenicin (1), isolated from

Novel carbocationic rearrangements of 1-styrylpropargyl alcohols

• Christine Basmadjian,
• Fan Zhang and
• Laurent Désaubry

Beilstein J. Org. Chem. 2015, 11, 1017–1022, doi:10.3762/bjoc.11.114

• : carbocationic rearrangement; cyclopentenones; furans; propargyl alcohols; Introduction In the course of our medicinal program on a new class of anticancer agents [1][2][3], we developed a novel synthesis of cyclopentenones substituted by three different aryl groups (Scheme 1) [4]. This approach combines a

Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products

• Sultan Taskaya,
• Nurettin Menges and
• Metin Balci

Beilstein J. Org. Chem. 2015, 11, 897–905, doi:10.3762/bjoc.11.101

• synthesis of pharmaceutically relevant building blocks has always been a significant goal in organic synthesis. Moreover, modification of natural products is also an important approach to identify promising anticancer agents. Especially due to the bioactivity of lukianols, many groups accomplished the

C-5’-Triazolyl-2’-oxa-3’-aza-4’a-carbanucleosides: Synthesis and biological evaluation

• Roberto Romeo,
• Caterina Carnovale,
• Salvatore V. Giofrè,
• Maria A. Chiacchio,
• Adriana Garozzo,
• Emanuele Amata,
• Giovanni Romeo and
• Ugo Chiacchio

Beilstein J. Org. Chem. 2015, 11, 328–334, doi:10.3762/bjoc.11.38

• structures in particular as antiviral or anticancer agents [1][2][3][4][5][6][7][8]. As analogues these compounds can interfere in nucleic acid synthesis or block nucleosides- and/or nucleotide-dependent biological processes by mimicking natural nucleosides and serving as inhibitors or building units [9][10

Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin

• Hale Ünal,
• Naile Öztürk and
• Erem Bilensoy

Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22

• consideration of the disadvantages that limit the effectiveness of oral chemotherapy and the advantages of nanoparticular drug delivery systems, developing a strategy with nanoparticles and even nanocapsules might be very promising for oral delivery of anticancer agents. Nanocapsules are especially beneficial

Formation of nanoparticles by cooperative inclusion between (S)-camptothecin-modified dextrans and β-cyclodextrin polymers

• Thorbjørn Terndrup Nielsen,
• Catherine Amiel,
• Laurent Duroux,
• Kim Lambertsen Larsen,
• Lars Wagner Städe,
• Reinhard Wimmer and
• Véronique Wintgens

Beilstein J. Org. Chem. 2015, 11, 147–154, doi:10.3762/bjoc.11.14

• the western world and approximately one out of four deaths is currently due to cancer [1]. Conventional chemotherapy is associated with severe adverse effects by the non-specific action of anticancer agents. Furthermore, many of highly promising novel anticancer agents fail to even reach clinical

Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”

• Julio Benites,
• Juan Meléndez,
• Cynthia Estela,
• David Ríos,
• Luis Espinoza,
• Iván Brito and
• Jaime A. Valderrama

Beilstein J. Org. Chem. 2014, 10, 2448–2452, doi:10.3762/bjoc.10.255

• of their properties as dyes for optical devices [15], antioxidants [16], anticancer agents [17] and precursors of liquid crystalline materials [18]. With regard to the synthesis of N-phenyl-1,4-naphthoquinone monoimines, Bukhtoyarova et al. [19], has described their preparation by reaction of 1,5-DHN

First synthesis of meso-substituted pyrrolo[1,2-a]quinoxalinoporphyrins

• Dileep Kumar Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2014, 10, 808–813, doi:10.3762/bjoc.10.76

• subunit display a wide spectrum of biological profiles as antagonists [26][27], PARP-1 inhibitors [28], anticancer agents [29][30], anti-HIV agents [31], and antimalarial agents [32][33]. These molecules are also important intermediates for the construction of 5-HT3 receptor agonists [34][35] and are

Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties

• Catalin V. Maftei,
• Elena Fodor,
• Peter G. Jones,
• M. Heiko Franz,
• Gerhard Kelter,
• Heiner Fiebig and
• Ion Neda

Beilstein J. Org. Chem. 2013, 9, 2202–2215, doi:10.3762/bjoc.9.259

• inducers represents an attractive approach for the discovery of new anticancer agents. 1,2,4-oxadiazole A (Figure 2) was found to act as an apoptosis agent by a high-throughput screening (HTS) assay [8]. A series of 1,2,4-oxadiazole-5-carboxamides B have been synthesized and tested as inhibitors of the

A study on electrospray mass spectrometry of fullerenol C₆₀(OH)₂₄

• Mihaela Silion,
• Andrei Dascalu,
• Mariana Pinteala,
• Bogdan C. Simionescu and
• Cezar Ungurenasu

Beilstein J. Org. Chem. 2013, 9, 1285–1295, doi:10.3762/bjoc.9.145

• ], neuroprotective [4][5][6][7], and anticancer agents [8][9][10][11][12][13], polyhydroxylated [C60]fullerenes, C60(OH)x, have received much attention in recent years. However, to the best of our knowledge, except for the compositionally and structurally well characterized C60(OH)24, prepared by alkaline hydrolysis

Simple synthesis of pyrrolo[3,2-e]indole-1-carbonitriles

• Adam Trawczyński,
• Robert Bujok,
• Zbigniew Wróbel and
• Krzysztof Wojciechowski

Beilstein J. Org. Chem. 2013, 9, 934–941, doi:10.3762/bjoc.9.107

• -dihydropyrrolo[3,2-e]indole fragment is present in anticancer agents, such as CC-1065 [1], duocarmycin [1], and yatakemycin [2]. Some pyrrolo[3,2-e]indole derivatives show antimicrobial activity [3]. One method of synthesis of the 1,2-dihydropyrrolo[2,3-e]indoles is reduction of pyrrolo[3,2-e]indoles with sodium

Formal synthesis of (−)-agelastatin A: an iron(II)-mediated cyclization strategy

• Daisuke Shigeoka,
• Takuma Kamon and
• Takehiko Yoshimitsu

Beilstein J. Org. Chem. 2013, 9, 860–865, doi:10.3762/bjoc.9.99

• isolated from marine sponges Agelas dendromorpha and Cymbastela sp., is one such substance, which has drawn considerable attention due to its potential applicability in the development of anticancer agents [1][2][3][4][5]. The intriguing biological activity of 1 has stimulated interest in developing

The diketopiperazine-fused tetrahydro-β-carboline scaffold as a model peptidomimetic with an unusual α-turn secondary structure

• Francesco Airaghi,
• Andrea Fiorati,
• Giordano Lesma,
• Manuele Musolino,
• Alessandro Sacchetti and
• Alessandra Silvani

Beilstein J. Org. Chem. 2013, 9, 147–154, doi:10.3762/bjoc.9.17

• attention in recent years because of their broad biological activities [11][12] and therapeutic applications, ranging from antibiotics [13] to anticancer agents [14]. Moreover, the DKP moiety has been exploited as a peptidomimetic scaffold [15][16][17]. Structural unification of THBC and DKP pharmacophores

A new synthetic access to 2-N-(glycosyl)thiosemicarbazides from 3-N-(glycosyl)oxadiazolinethiones and the regioselectivity of the glycosylation of their oxadiazolinethione precursors

• El Sayed H. El Ashry,
• El Sayed H. El Tamany,
• Mohy El Din Abdel Fattah,
• Mohamed R. E. Aly,
• Ahmed T. A. Boraei and
• Axel Duerkop

Beilstein J. Org. Chem. 2013, 9, 135–146, doi:10.3762/bjoc.9.16

• acid. This is known as a metabolic cell-surface-engineering technique for cell-surface interactions and consequently shows the potential of these compounds for the development of anticancer agents [13][14][15][16]. Antituberculosis effects of glycosylthiosemicarbazides were also reviewed [17

Bioactive selaginellins from Selaginella tamariscina (Beauv.) Spring

• Chao Yang,
• Yutian Shao,
• Kang Li and
• Wujiong Xia

Beilstein J. Org. Chem. 2012, 8, 1884–1889, doi:10.3762/bjoc.8.217

• were assigned in Table 2. Several species of the genus Selaginella have long been used in traditional medicine as anticancer agents, but only limited literature information on the cytotoxic activity of their constituents is available, which encourages us to investigate the cytotoxic effect of the

• more potent and selective selaginellin analogues and their biogenetic precursors. Additional controlled studies are needed to investigate the efficacy and safety of selaginellins as antioxidant and anticancer agents. Experimental General experimental procedures. IR spectra were measured on a Perkin