New Amino-Bisphosphonate Building Blocks in the Synthesis of Bisphosphonic Derivatives Based on Lead Compounds

Becker, Christina S.; Чуканов, Н. В.; Григорьев, И. А.

doi:10.1080/10426507.2014.979989

Cited by 6 publications

(5 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“… (3β)-28-[(2-Aminoethyl)amino]-28-oxours-12-en-3-yl acetate ( 18 ). This compound (0.81 g, 87%) was obtained from 2 following GPB as a colorless solid; [ 37 , 38 , 39 , 40 ] m.p. 202–205 °C (lit.…”

Section: Methodsmentioning

confidence: 99%

“…This compound (0.69 g, 83%) was obtained from 1 following GPB as a colorless solid; [35,36] (3β)-28-[(2-Aminoethyl)amino]-28-oxours-12-en-3-yl acetate (18). This compound (0.81 g, 87%) was obtained from 2 following GPB as a colorless solid; [37][38][39][40] (3β)-28-Oxo-piperazin-1-yl-olean-12-en-3-yl acetate (21). This compound (0.91 g, 92%) was obtained from 1 following GPB as a colorless solid; [43][44][45][46] (3β)-28-Oxo-piperazin-1-yl-ursan-12-en-3-yl acetate (22).…”

Section: General Procedures For the Synthesis Of Amides 9-31 (Gpb)mentioning

confidence: 99%

See 1 more Smart Citation

The Presence of a Cyclohexyldiamine Moiety Confers Cytotoxicity to Pentacyclic Triterpenoids

et al. 2021

View full text Add to dashboard Cite

Pentacyclic triterpenoids oleanolic acid, ursolic acid, betulinic acid, and platanic acid were acetylated and converted into several amides 9–31; the cytotoxicity of which has been determined in sulforhodamine B assays employing seral human tumor cell lines and nonmalignant fibroblasts. Thereby, a betulinic acid/trans-1,4-cyclohexyldiamine amide showed excellent cytotoxicity (for example, EC50 = 0.6 μM for HT29 colon adenocarcinoma cells).

show abstract

Section: Methodsmentioning

confidence: 99%

Section: General Procedures For the Synthesis Of Amides 9-31 (Gpb)mentioning

confidence: 99%

The Presence of a Cyclohexyldiamine Moiety Confers Cytotoxicity to Pentacyclic Triterpenoids

et al. 2021

View full text Add to dashboard Cite

show abstract

“…There are two main methodologies to prepare BA/BoA/HBA-based amide derivatives at position 28 [15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30]. The first methodology is based on the formation of an acyl chloride (RCOCl, R = BA/BoA/HBA) as key intermediate using oxalyl chloride [(CO) 2 Cl 2 ], followed by amination reactions with primary or secondary amines usually in the presence of a base (e.g., Et 3 N).…”

Section: Simple Transformationsmentioning

confidence: 99%

“…Becker et al prepared aminobisphosphonate‒BoA 15 and aminobisphosphonate‒BA 16 conjugates, using the methodology described above, in order to obtain potential anticancer agents [23]. Conjugate 15 was synthesized in 89% yield through the reaction of BoA chloride 7 with tetraethyl 1-(2-aminoethylamino)ethane-1,1-diyldiphosphonate in the presence of Et 3 N (Scheme 3).…”

Section: Simple Transformationsmentioning

confidence: 99%

Recent Developments in the Functionalization of Betulinic Acid and Its Natural Analogues: A Route to New Bioactive Compounds

et al. 2019

View full text Add to dashboard Cite

Betulinic acid (BA) and its natural analogues betulin (BN), betulonic (BoA), and 23-hydroxybetulinic (HBA) acids are lupane-type pentacyclic triterpenoids. They are present in many plants and display important biological activities. This review focuses on the chemical transformations used to functionalize BA/BN/BoA/HBA in order to obtain new derivatives with improved biological activity, covering the period since 2013 to 2018. It is divided by the main chemical transformations reported in the literature, including amination, esterification, alkylation, sulfonation, copper(I)-catalyzed alkyne-azide cycloaddition, palladium-catalyzed cross-coupling, hydroxylation, and aldol condensation reactions. In addition, the synthesis of heterocycle-fused BA/HBA derivatives and polymer‒BA conjugates are also addressed. The new derivatives are mainly used as antitumor agents, but there are other biological applications such as antimalarial activity, drug delivery, bioimaging, among others.

show abstract

“…Studies of their photopolymerization indicated that they may be suitable for potential use in dentistry. Using DCC as a coupling agent, diethyl 1-(2-aminoethylamino)-1,1-ethylbisphosphonate was acylated by structurally variable natural acids, such as folic acid [140,141], ursulonic and betulinic acids [142], and trolox [141,143].…”

Section: Synthesis Of Building Blocks For Polymer Chemistrymentioning

confidence: 99%

Synthetic Procedures Leading towards Aminobisphosphonates

Chmielewska

Kafarski

2016

Molecules

View full text Add to dashboard Cite

Abstract:Growing interest in the biological activity of aminobisphosphonates has stimulated the development of methods for their synthesis. Although several general procedures were previously elaborated to reach this goal, aminobisphosphonate chemistry is still developing quite substantially. Thus, innovative modifications of the existing commonly used reactions, as well as development of new procedures, are presented in this review, concentrating on recent achievements. Additionally, selected examples of aminobisphosphonate derivatization illustrate their usefulness for obtaining new diagnostic and therapeutic agents.

show abstract

New Amino-Bisphosphonate Building Blocks in the Synthesis of Bisphosphonic Derivatives Based on Lead Compounds

Cited by 6 publications

References 51 publications

The Presence of a Cyclohexyldiamine Moiety Confers Cytotoxicity to Pentacyclic Triterpenoids

The Presence of a Cyclohexyldiamine Moiety Confers Cytotoxicity to Pentacyclic Triterpenoids

Recent Developments in the Functionalization of Betulinic Acid and Its Natural Analogues: A Route to New Bioactive Compounds

Synthetic Procedures Leading towards Aminobisphosphonates

Contact Info

Product

Resources

About