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Search for "antitumor" in Full Text gives 279 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

  • Silvie Rimpelová,
  • Michal Jurášek,
  • Lucie Peterková,
  • Jiří Bejček,
  • Vojtěch Spiwok,
  • Miloš Majdl,
  • Michal Jirásko,
  • Miloš Buděšínský,
  • Juraj Harmatha,
  • Eva Kmoníčková,
  • Pavel Drašar and
  • Tomáš Ruml

Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189

Graphical Abstract
  • antitumor (thapsigargin; [25]) agents or have been experimentally investigated with an increasing rate (see PubMed results by year). In order to assess the immunobiological potential of compound 1, its cytotoxicity had to be determined first. Therefore, we measured its impact on the viability of rat
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Published 13 Aug 2019

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

  • András György Németh,
  • György Miklós Keserű and
  • Péter Ábrányi-Balogh

Beilstein J. Org. Chem. 2019, 15, 1523–1533, doi:10.3762/bjoc.15.155

Graphical Abstract
  • ; multicomponent reaction; one-pot; thiocarbamate; Introduction O-Thiocarbamates belong to a class of important biologically active molecules, used mainly as fungicides [1][2][3] in agricultural and pharmaceutical fields. In particular, recently antitumor [4], anesthetic [5] and enzyme inhibitory effects were
  • as enzyme inhibitors [26] or antitumor agents [27]. These species are also used as valuable synthetic intermediates [28] and chemosensors for mercury and silver [29][30]. The general methods for the synthesis of O-thiocarbamates and dithiocarbamates traditionally rely on substitution reactions of the
  • ), a new quinazolinone derivative in 40% yield (Scheme 6). Notably, these heterocycles are known for their use as antitumor [101], anticonvulsant [102] or epidermal growth factor receptor tyrosine kinase inhibitory agents [103], JNK inhibitors [104] or 5-HT3 antagonists [105]. Earlier, a one-pot
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Published 10 Jul 2019

A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water

  • Piyali Sarkar,
  • Sayan Sarkar and
  • Pradyut Ghosh

Beilstein J. Org. Chem. 2019, 15, 1505–1514, doi:10.3762/bjoc.15.152

Graphical Abstract
  • antitumor, antifungal, anthelmintic, anticancer activities, etc. [5][6][7]. Although a few syntheses of these molecules have been reported in the literature, these generally consist of multistep protocols and require harsh acidic catalysts [5][8][9][10][11][12]. Moreover, only in a very few cases, the
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Published 08 Jul 2019

Efficiency Effsyn of complex syntheses as multicomponent reactions, its algorithm and calculations based on concrete criteria

  • Heiner Eckert

Beilstein J. Org. Chem. 2019, 15, 1425–1433, doi:10.3762/bjoc.15.142

Graphical Abstract
  • components for linking, and also generates its own structure which is capable of extensions like the domino reaction types [5]. An Ugi reaction is used in the total synthesis of the extremely potent antitumor agent ecteinascidin-743 (Et-743, 1) by Fukuyama to form a large part of the skeleton 2 (Scheme 5
  • : novel MCR as key step in total synthesis of (+)-20S-camptothecin Another typical example for the simplification of a complex chemical synthesis [2][3] is the total synthesis of the extremely potent antitumor agent (+)-20S-camptothecin (3), which has been a highly effective agent for decades now. This
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Published 27 Jun 2019

Anomeric sugar boronic acid analogues as potential agents for boron neutron capture therapy

  • Daniela Imperio,
  • Erika Del Grosso,
  • Silvia Fallarini,
  • Grazia Lombardi and
  • Luigi Panza

Beilstein J. Org. Chem. 2019, 15, 1355–1359, doi:10.3762/bjoc.15.135

Graphical Abstract
  • position. The analogues were obtained by hydroboration of proper open-chain terminal alkenes that, after quenching with water, spontaneously afforded cyclic boronic acids with hemiacetal-like structures. Keywords: antitumor agents; boron neutron capture therapy; boronic acid; hydroboration; sugar analogue
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Published 19 Jun 2019

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

  • Victoria V. Lipson,
  • Tetiana L. Pavlovska,
  • Nataliya V. Svetlichnaya,
  • Anna A. Poryvai,
  • Nikolay Yu. Gorobets,
  • Erik V. Van der Eycken,
  • Irina S. Konovalova,
  • Svetlana V. Shiskina,
  • Alexander V. Borisov,
  • Vladimir I. Musatov and
  • Alexander V. Mazepa

Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

Graphical Abstract
  • antagonists [8], cyclin-dependent kinases GSK-3β, CK1 [9] and nitric oxide synthase activity inhibitors [10][11], as well as antibacterial [2], antifungal [12], antihistamine [13] and antitumor activities [14]. Remarkable immunosuppressive properties are inherent to palau’amine (VI) [15]. Ceratamines XIII are
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Published 06 May 2019

Diastereo- and enantioselective preparation of cyclopropanol derivatives

  • Marwan Simaan and
  • Ilan Marek

Beilstein J. Org. Chem. 2019, 15, 752–760, doi:10.3762/bjoc.15.71

Graphical Abstract
  • transformations [1]. The cyclopropane subunit is also present in many biologically important compounds such as pheromones, fatty acid metabolites, unusual amino acids and possess interesting herbicidal, insecticidal, antibiotic, antibacterial, antifungal, antiviral and antitumor activities [2]. For these reasons
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Published 21 Mar 2019

Efficient synthesis of 4-substituted-ortho-phthalaldehyde analogues: toward the emergence of new building blocks

  • Clémence Moitessier,
  • Ahmad Rifai,
  • Pierre-Edouard Danjou,
  • Isabelle Mallard and
  • Francine Cazier-Dennin

Beilstein J. Org. Chem. 2019, 15, 721–726, doi:10.3762/bjoc.15.67

Graphical Abstract
  • -methoxy-ortho-xylene in only 5% yield [14]. 4-HO-OPA was also described in 1997 by Taylor et al. as a crude product (via a Diels–Alder reaction of commercially available Danishefsky diene with 4,4-diethoxybut-2-ynal) for the synthesis of an antitumor analogue [15]. This aforementioned strategy was applied
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Published 19 Mar 2019

Synthesis and biological investigation of (+)-3-hydroxymethylartemisinin

  • Toni Smeilus,
  • Farnoush Mousavizadeh,
  • Johannes Krieger,
  • Xingzhao Tu,
  • Marcel Kaiser and
  • Athanassios Giannis

Beilstein J. Org. Chem. 2019, 15, 567–570, doi:10.3762/bjoc.15.51

Graphical Abstract
  • sesquiterpene lactone is still unknown [5]. Whereas artemisinins are almost non-toxic to normal cells, several studies have confirmed their potent antitumor activity [6][7]. In addition, they have been reported to possess immunosuppressive, anti-inflammatory, antiviral, antifungal and antiparasitic activities
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Published 27 Feb 2019

Selectivity in multiple multicomponent reactions: types and synthetic applications

  • Ouldouz Ghashghaei,
  • Francesca Seghetti and
  • Rodolfo Lavilla

Beilstein J. Org. Chem. 2019, 15, 521–534, doi:10.3762/bjoc.15.46

Graphical Abstract
  • antitumor peptidomimetics (Scheme 16) [53]. The convergent approach employs three different isocyanide-MCRs, efficiently prepares the building blocks and combines them, intercalating protecting group cleavages. Conclusion The MMCRs approach represents the most efficient way to build chemical complexity and
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Published 21 Feb 2019

Reusable and highly enantioselective water-soluble Ru(II)-Amm-Pheox catalyst for intramolecular cyclopropanation of diazo compounds

  • Hamada S. A. Mandour,
  • Yoko Nakagawa,
  • Masaya Tone,
  • Hayato Inoue,
  • Nansalmaa Otog,
  • Ikuhide Fujisawa,
  • Soda Chanthamath and
  • Seiji Iwasa

Beilstein J. Org. Chem. 2019, 15, 357–363, doi:10.3762/bjoc.15.31

Graphical Abstract
  • nature and have excellent biological activity, including strong antibiotic, antihelmetic, antifungal, antitumor, antiviral and anti-inflammatory, which make them interesting lead structures for new drugs [34]. That is why a great deal of attention has been paid to the synthesis of the lactone ring [35
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Published 06 Feb 2019

Olefin metathesis in multiblock copolymer synthesis

  • Maria L. Gringolts,
  • Yulia I. Denisova,
  • Eugene Sh. Finkelshtein and
  • Yaroslav V. Kudryavtsev

Beilstein J. Org. Chem. 2019, 15, 218–235, doi:10.3762/bjoc.15.21

Graphical Abstract
  • functionalized with N-hydroxysuccinate esters (NHS) that can be used as a carrier for antitumor drugs, and the C block is a far-red emitting conjugated random copolymer of p-phenylene ethynylene (PPE) and perylene monoimide (PMI, Figure 2). For the synthesis, the random PPE–PMI copolymer was end-capped with
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Published 24 Jan 2019

Synthesis of a tubugi-1-toxin conjugate by a modulizable disulfide linker system with a neuropeptide Y analogue showing selectivity for hY1R-overexpressing tumor cells

  • Rainer Kufka,
  • Robert Rennert,
  • Goran N. Kaluđerović,
  • Lutz Weber,
  • Wolfgang Richter and
  • Ludger A. Wessjohann

Beilstein J. Org. Chem. 2019, 15, 96–105, doi:10.3762/bjoc.15.11

Graphical Abstract
  • doxorubicin as cytotoxic drugs to native NPY by using various linker chemistries. However, due to missing hY1R-selectivity and relatively weak antitumor efficacy these conjugates were found unsuitable as PDCs [38]. More recently, further approaches of hY1R-addressing PDCs for therapeutic applications have
  • cells. Hence, these toxins primarily affect fast dividing cells, for instance all active cancer cells. Tubugis as derivatives of natural tubulysins have an almost identical antitumor activity, but are readily available and, most importantly, are chemically more inert and less degradable than native
  • with respect to the antitumor impact of the peptide–toxin conjugate 8. Effect on cell viability and proliferation Due to their very high toxic potency, tubulysins as well as their synthetic tubugi analogues can also exhibit toxic effects on healthy cells. Therefore, considerable adverse effects can
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Published 10 Jan 2019

Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines

  • Olga A. Storozhenko,
  • Alexey A. Festa,
  • Delphine R. Bella Ndoutoume,
  • Alexander V. Aksenov,
  • Alexey V. Varlamov and
  • Leonid G. Voskressensky

Beilstein J. Org. Chem. 2018, 14, 3078–3087, doi:10.3762/bjoc.14.287

Graphical Abstract
  • may be found in crolibulin, an antitumor agent, undergoing phase II clinical trials [31], chromenotacrine CT-6, a potential anti-Alzheimer agent [32], and pranoprofen, a marketed anti-inflammatory drug [33]. Combination of chromene and imidazopyridine rings led to the discovery of compound A with
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Published 19 Dec 2018

Repurposing the anticancer drug cisplatin with the aim of developing novel Pseudomonas aeruginosa infection control agents

  • Mingjun Yuan,
  • Song Lin Chua,
  • Yang Liu,
  • Daniela I. Drautz-Moses,
  • Joey Kuok Hoong Yam,
  • Thet Tun Aung,
  • Roger W. Beuerman,
  • May Margarette Santillan Salido,
  • Stephan C. Schuster,
  • Choon-Hong Tan,
  • Michael Givskov,
  • Liang Yang and
  • Thomas E. Nielsen

Beilstein J. Org. Chem. 2018, 14, 3059–3069, doi:10.3762/bjoc.14.284

Graphical Abstract
  • compounds in both academia and the pharmaceutical industry. Here, we report how the widely used antitumor drug cisplatin may be repurposed as an effective antimicrobial against the nosocomial pathogen Pseudomonas aeruginosa. Cisplatin was found to effectively kill strains of P. aeruginosa. In such
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Published 14 Dec 2018

Synthesis of dihydroquinazolines from 2-aminobenzylamine: N3-aryl derivatives with electron-withdrawing groups

  • Nadia Gruber,
  • Jimena E. Díaz and
  • Liliana R. Orelli

Beilstein J. Org. Chem. 2018, 14, 2510–2519, doi:10.3762/bjoc.14.227

Graphical Abstract
  • pharmacological interest. For example, vasicine is a 3,4-dihydroquinazoline alkaloid isolated from natural sources with antitumor activity [1]. Vasicine and deoxyvasicine are also potent butyrylcholinesterase (BChE) inhibitors [2]. Some synthetic derivatives containing the dihydroquinazoline scaffold have shown
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Published 26 Sep 2018

Comparative cell biological study of in vitro antitumor and antimetastatic activity on melanoma cells of GnRH-III-containing conjugates modified with short-chain fatty acids

  • Eszter Lajkó,
  • Sarah Spring,
  • Rózsa Hegedüs,
  • Beáta Biri-Kovács,
  • Sven Ingebrandt,
  • Gábor Mező and
  • László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 2495–2509, doi:10.3762/bjoc.14.226

Graphical Abstract
  • melanoma cells was increased by [4Lys(Ac)]-GnRH-III(Dau=Aoa), while the GnRH-III(Dau=Aoa) and [4Lys(Bu)]-GnRH-III(Dau=Aoa) decreased this activity. Conclusion: Internalization and cytotoxicity of the conjugates showed that GnRH-III peptides could guard Dau to melanoma cells and promote antitumor activity
  • doxorubicin (formerly known as AEZS-108 or AN-152), in which the superagonist [D-6Lys]-GnRH-I allows the tumor targeting of the traditional chemotherapeutical drug doxorubicin covalently linked via an ester bond [3][10]. However, while in the phase II trial, zoptarelin doxorubicin showed promising antitumor
  • most potent one in all different assays (enzymatic stability, cellular uptake, and in vitro antitumor activity) on HT-29 colon carcinoma cell lines [19]. The different hydrophobicity of conjugates having a short, fatty acid side chain (2–6 carbon atoms) could be excluded as an explanation for their
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Published 26 Sep 2018

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

  • Sambasivarao Kotha,
  • Milind Meshram and
  • Chandravathi Chakkapalli

Beilstein J. Org. Chem. 2018, 14, 2468–2481, doi:10.3762/bjoc.14.223

Graphical Abstract
  • CM by using Mo complex 6. In this regard, they assembled stilbene derivative 85 as an antitumor agent by a two-step strategy that involve catalytic CM and SM coupling. To this end, the Z-selective CM of a styrene derivative (e.g., 81) with vinyl-B(pin) 82 was realized in the presence of Mo complex 6
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Published 21 Sep 2018

Strong binding and fluorescence sensing of bisphosphonates by guanidinium-modified calix[5]arene

  • Jie Gao,
  • Zhe Zheng,
  • Lin Shi,
  • Si-Qi Wu,
  • Hongwei Sun and
  • Dong-Sheng Guo

Beilstein J. Org. Chem. 2018, 14, 1840–1845, doi:10.3762/bjoc.14.157

Graphical Abstract
  • , hypercalcaemia and bone pain caused by bone metastases of malignant tumors [2][3]. In addition, BPs are increasingly considered due to their potential role in preventing and treating cancer-induced bone loss and antitumor effects [4][5]. With this regard, assays for BPs are significant for identifying the
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Published 19 Jul 2018

Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

  • Fateh V. Singh,
  • Priyanka B. Kole,
  • Saeesh R. Mangaonkar and
  • Samata E. Shetgaonkar

Beilstein J. Org. Chem. 2018, 14, 1778–1805, doi:10.3762/bjoc.14.152

Graphical Abstract
  • starting from catechol derivative 142. Marine sesquiterpenoids are mainly known for their biological importance such as antitumor, antiviral and antibiotic properties [132]. In this report, the catechol-derived starting substrate 142 was cyclized to spirocyclic product 143 in 67% yield using PIFA (31) as
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Published 17 Jul 2018

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

Graphical Abstract
  • ., Dec-NH2, [Pro]4-Dec-NH2, [Arg]1-Dec-NH2, [Phe]2-Dec-NH2 and [Phe]6-Des[Thr]11-Dec-NH2. The analogs presented similar antitumor activity in growth inhibition assays with MCF-7 breast cancer cells. Dec-NH2, Trp- and Phe-substituted analogs were described as the most hemolytic peptides of their family
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Published 06 Jul 2018

β-Hydroxy sulfides and their syntheses

  • Mokgethwa B. Marakalala,
  • Edwin M. Mmutlane and
  • Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1668–1692, doi:10.3762/bjoc.14.143

Graphical Abstract
  • architectural extreme are: the ecteinascidins, antitumor tetrahydroisoquinoline alkaloids from the colonial Ascidian Ecteinascidia turbinata as exemplified by ecteinascidin 729 (4) [6]; ulbactins F (5a) and G (5b), two polycyclic thiazoline congeners isolated from a culture extract of a sponge derived
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Published 05 Jul 2018

Anomeric modification of carbohydrates using the Mitsunobu reaction

  • Julia Hain,
  • Patrick Rollin,
  • Werner Klaffke and
  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1619–1636, doi:10.3762/bjoc.14.138

Graphical Abstract
  • synthesis of phyllanthostatin antitumor agents, A. B. Smith and colleagues soundly investigated the suitability of the Mitsunobu reaction [29]. They concluded already back in 1986 that “the anomeric hydroxyl group of various pyranose hemiacetals can be esterified with inversion of configuration
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Published 29 Jun 2018

Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

  • Yuichi Yoshimura,
  • Hideaki Wakamatsu,
  • Yoshihiro Natori,
  • Yukako Saito and
  • Noriaki Minakawa

Beilstein J. Org. Chem. 2018, 14, 1595–1618, doi:10.3762/bjoc.14.137

Graphical Abstract
  • , we have steadily pursued the identification of novel antitumor and antiviral nucleoside derivatives [17][20][21][22]. Matsuda and co-workers reported a 2’-substituted cytidine derivative, DMDC (1), with potent antitumor activity [23][24]. In other reports, Walker [25] and Secrist [26] independently
  • promising candidates for novel antitumor agents. Thus, we designed a novel 2’-substituted 4’-thiocytidine, 4’-thioDMDC (3), as our target molecule for potential antitumor agents [27][28] (Figure 1). At the time we started our project, there had been no reports regarding the synthesis of even 2-substituted 4
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Published 28 Jun 2018

Drug targeting to decrease cardiotoxicity – determination of the cytotoxic effect of GnRH-based conjugates containing doxorubicin, daunorubicin and methotrexate on human cardiomyocytes and endothelial cells

  • Livia Polgár,
  • Eszter Lajkó,
  • Pál Soós,
  • Orsolya Láng,
  • Marilena Manea,
  • Béla Merkely,
  • Gábor Mező and
  • László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 1583–1594, doi:10.3762/bjoc.14.136

Graphical Abstract
  • cytotoxic effect on cardiomyocytes were identified. In the future, these compounds could provide a more targeted antitumor therapy with no cardiotoxic adverse effects. Moreover, impedimetric cytotoxicity analysis could be a valuable technique to determine the effect of drugs on cardiomyocytes. Keywords
  • the pituitary [4]. GnRH-III (Glp-His-Trp-Ser-His-Trp-Lys-Pro-Gly-NH2, where Glp is pyroglutamic acid) is a naturally occurring isoform of GnRH, which was first isolated from sea lamprey [5]. GnRH-III has been shown to exert an effective antitumor activity against a number of tumor types [6][7][8
  • technique of high interest, by which cytotoxic drugs are attached to specific molecules (homing devices) with the aim of increasing the accumulation of the drug in the specific target cells. Consequently, this leads to a more efficient antitumor effect and to the reduction of potential adverse side effects
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Published 28 Jun 2018
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