Guanylated Diamines, Triamines, and Polyamines: Chemistry and Biological Properties

Castagnolo, Daniele; Schenone, Silvia; Botta, Maurizio

doi:10.1021/cr100423x

Cited by 101 publications

(56 citation statements)

References 233 publications

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“…Please note that, depending on the substituents R, R′, and R′′, several isomers (tautomers) are conceivable. Mono‐ (R=R′=R′′=H) and persubstituted (R or R′ or R′′≠H) bis(guanidine)s are beyond the scope of this review, but have been discussed elsewhere, wherefore compounds with one to three hydrogen atoms per guanidine unit are discussed in the following.…”

Section: Bis(guanidine)smentioning

confidence: 99%

“…[59, 60a] In the second approach (ix), ab is(carbodiimide), which is either generated from the bis(thiourea) or from bis(iminophosphorane), is reacted with an excess of amine yieldingt he related macrocyclic bis(guanidine)si nv ery good yields. [75] Compared with bis(amidine)s, bis(guanidine)s found multifarious applicationsa sc atalysts, [59,76] ions ensors, [60] pharmaceuticals, [63] or superbases. [61] To some extent, bis(guanidine) complexes (Figure 15) resemble the coordination patterns observed for bis(amidinate)s. Mononuclear complexes of type A are known for Eu, [77] Nd, [78] Sm, [79] Ta, [80] Ti, [68b] Y, [78,81] Yb, [78,81,82] Zr, [68b] and have been either directly derived from the bis(guanidine) [68b] or from in situ generated dinuclearalkali-metal complexes, [77][78][79][80][81] which are readily accessible from the reactiono f metallated secondary diamines with two equivalents of ac ar- Review bodiimide.…”

Section: Bis(guanidine)smentioning

confidence: 99%

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Ligands with Two Monoanionic N,N‐Binding Sites: Synthesis and Coordination Chemistry

Kretschmer

2019

Chemistry A European J

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Polytopic ligands have become ubiquitous in coordination chemistry because they grant access to a variety of mono‐ and polynuclear complexes of transition metals as well as rare‐earth and main‐group elements. Nitrogen‐based ditopic ligands, in which two monoanionic N,N‐binding sites are framed within one molecule, are of particular importance and are therefore the primary focus of this review. In detail, bis(amidine)s, bis(guanidine)s, bis(β‐diimine)s, bis(aminotroponimine)s, bis(pyrrolimine)s, and miscellaneous bis(N,N‐chelating) ligands are reviewed. In addition to the general synthetic protocols, the application of these ligands is discussed along with their coordination chemistry, the multifarious binding modes, and the ability of these ligands to bridge two (or more) metal(loids).

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Section: Bis(guanidine)smentioning

confidence: 99%

Section: Bis(guanidine)smentioning

confidence: 99%

Ligands with Two Monoanionic N,N‐Binding Sites: Synthesis and Coordination Chemistry

Kretschmer

2019

Chemistry A European J

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“…[9][10] We recently discovered both macrocyclic and linear amidinurea derivatives endowed with antifungal 11 and antiviral activity. 12 Some amidinurea derivatives also showed anti-proliferative properties 13 probably due to their ability to mimicking the natural nucleobases and thus to interact with DNA.…”

Section: D (N-[n-[8-[[n-(morpholine-4-carbonyl)carbamimidoyl] Amino]mentioning

confidence: 99%

Synthesis and Biological Evaluation of Amidinourea and Triazine Congeners as Inhibitors of MDA‐MB‐231 Human Breast Cancer Cell Proliferation

et al. 2017

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“…The guanidine group is a common key unit in various natural and synthetic compounds demonstrating antimicrobial, antiviral, and antitumor activities [11]. Furthermore, because of high basicity (pKa 13.5), the guanidinium group is important for selective delivery of cytotoxic molecules to tumor cells [12].…”

Section: Introductionmentioning

confidence: 99%

C-28 Esters of Triterpenoid Acids Bearing Tris(hydroxymethyl)aminomethane: Synthesis and Anticancer/Antimicrobial Activity

Spivak

Nedopekina

Dzhemileva

et al. 2019

The 23rd International Electronic Conference on Synthetic Organic Chemistry

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Widespread secondary plant metabolites (betulinic, ursolic, and oleanolic acids) are promising scaffolds for the discovery of new drugs. Among the many semi-synthetic derivatives of lupane triterpenoids known today, the anticancer agent C-28 ester of betulinic acid with tris(hydroxymethyl)aminomethane (NVX-207) has been actively studied. This betulinic acid derivative, which has shown significant antitumor activity in vitro and in vivo against various malignant tumors, is a candidate drug. It is known that modification of the structure of the triterpenoid skeleton can lead to significant changes in biological properties. In this regard, we have synthesized C-28 esters of ursolic and oleanolic acids and C20-29 hydrogenated betulinic acid bearing tris(hydroxymethyl)aminomethane (TRIS), and transformed them into guanidinium salts by guanylation of the primary amino group in a branched ester fragment under the action of 1H-pyrazole-1-carboxamidine hydrochloride. The obtained compounds were tested in in vitro experiments on three human cancer cell lines. The presence of the TRIS-fragment in the triterpenoid conjugates markedly enhanced the cytotoxic action as compared to the parent compounds, dihydrobetulinic, ursolic, and oleanolic acids (IC50 values 2.8-7.6 μM for Jurkat cells and 1.1-6.8 μM for U937 cells), while the correlation between the cytotoxic activity and the chemical structure of the triterpenoid skeleton was not observed. Extended biological testing of these triterpenoids by using flow cytometry analysis showed that antitumor activity of compounds is caused by apoptotic processes and induction of cell cycle arrest in the S-phase. New triterpenoids were also tested for their antimicrobial activity against the growth of four bacterial strains (Escherichia coli, Acinetobacter baumannii, Pseudomonas aeruginosa, and Staphylococcus aureus (MRSA)) and two fungal strains (Candida albicans and Cryptococcus neoformans). The TRIS-dihydrobetulinic acid conjugate and its guanidinium derivative did not exhibit antimicrobial properties. The corresponding ursane and oleane-skeleton pentacyclic tritrerpenoids showed good bacteriostatic activity against methicillin-resistant S. aureus (MICs 4 and 32 μg/mL) and excellent antifungal effect against Cryptococcus neoformans and Candida albicans (MICs 4 and 0.25 μg/mL).

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Guanylated Diamines, Triamines, and Polyamines: Chemistry and Biological Properties

Cited by 101 publications

References 233 publications

Ligands with Two Monoanionic N,N‐Binding Sites: Synthesis and Coordination Chemistry

Ligands with Two Monoanionic N,N‐Binding Sites: Synthesis and Coordination Chemistry

Synthesis and Biological Evaluation of Amidinourea and Triazine Congeners as Inhibitors of MDA‐MB‐231 Human Breast Cancer Cell Proliferation

C-28 Esters of Triterpenoid Acids Bearing Tris(hydroxymethyl)aminomethane: Synthesis and Anticancer/Antimicrobial Activity

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