Steroidal esters of the aromatic nitrogen mustard 2-[4-N,N-bis(2-chloroethyl)amino-phenyl]butanoic acid (2-PHE-BU)

Papaconstantinou, Ioanna C.; Fousteris, Manolis A.; Koutsourea, Anna I.; Pairas, George; Παπαγεωργίου, Αθανάσιος; Nikolaropoulos, Sotiris S.

doi:10.1097/cad.0b013e328357f687

Cited by 12 publications

(8 citation statements)

References 32 publications

(48 reference statements)

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“…N , N ‐bis(2‐chloroethyl)‐1,4‐phenylenediamine, which belongs to aromatic N ‐mustard, has been researched in antitumor field for its good performance . It was found that the length of the spacer between the carrier part and alkylating part could influence their antitumor potency.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and cytotoxicity of pentacyclic triterpenes‐aniline nitrogen mustard derivatives

Liu

Tian

et al. 2019

J Chinese Chemical Soc

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To discover novel nitrogen mustards, the reported mustard pharmacophore was combined with natural pentacyclic triterpenes, which are characterized with pharmacological and structural diversity. Thus, six conjugates were synthesized with 1,2,3-triazole linking N,N-bis (2-chloroethyl)-1,4-phenylenediamine and oleanolic acid, ursolic acid, or glycyrrhetinic acid, and their biological activity was evaluated against tumor cell lines HeLa, BGC-823, BEL-7404, and NCI-H460 using the MTT assay. As a result, these conjugates showed some selective cytotoxicity to NCI-H460, though all their activity potency was moderate or weak in the four cell lines. K E Y W O R D S N,N-bis (2-chloroethyl)-1,4-phenylenediamine, nitrogen mustards, pentacyclic triterpenes Chun-Mei Liu and Xiao-Yan Tian contributed equally to this study.

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Section: Introductionmentioning

confidence: 99%

Synthesis and cytotoxicity of pentacyclic triterpenes‐aniline nitrogen mustard derivatives

Liu

Tian

et al. 2019

J Chinese Chemical Soc

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“…Chlorambucil is a DNA alkylating agent belonging to the nitrogen mustard class of anticancer agents; it can form covalent adducts with the nucleobases of the DNA, alkylating the nucleobases adenine and guanine at the nitrogens N3 and N7 [18,19]. As in the case of cisplatin, DNA cross-linking induced by chlorambucil prevents DNA replication and transcription, leading to cell death (Scheme 1) [20,21,22].…”

Section: Introductionmentioning

confidence: 99%

A Pt(IV) Prodrug Combining Chlorambucil and Cisplatin: A Dual-Acting Weapon for Targeting DNA in Cancer Cells

Montagner

Tolan

Andriollo

et al. 2018

IJMS

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In this study, two DNA-targeting agents, cisplatin and chlorambucil, were combined in a Pt(IV) prodrug, 1, which was thoroughly characterized by means of spectroscopic and spectrometric techniques. Tested towards a panel of various human tumor cell lines, this compound showed superior in vitro antitumor potential than the reference drug cisplatin. In addition, an antitumor potential of 1 was found, which is comparable to that of oxaliplatin in 3D spheroid models of colon cancer cells. Mechanistic studies performed in colon cancer cells confirmed that the conjugation of chlorambucil to Pt(IV) cisplatin-based scaffold tunes the lipophilicity of the prodrug, consequently improving the ability of the compound to accumulate into cancer cells and to target DNA, ultimately leading to apoptotic cancer cell death.

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“…Despite their lethal properties, mustard gases have attracted a great interest as versatile electrophiles in inorganic and organic synthesis also employed for the preparation of numerous pharmaceutical intermediates …”

Section: Introductionmentioning

confidence: 99%

β-Aminocarbonates in Regioselective and Ring Expansion Reactions

et al. 2017

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The reactivity of β-aminocarbonates as anisotropic electrophiles has been investigated with several phenols. Products distribution shows that the regioselectivity of the anchimerically driven alkylation reaction depends on the nucleophiles. The results suggest that in the presence of nucleophiles that are also good leaving groups, the reaction takes place under thermodynamic control favoring the attack on the most sterically hindered carbon of the cyclic aziridinium intermediate. Furthermore, when an enantiomerically pure pyrrolidine-based carbonate was used, the reaction with phenols proceeds via a bicyclic aziridinium intermediate leading to the stereoselective synthesis of optically active 3-substituted piperidines via ring expansion reaction. These results were confirmed both by NMR spectroscopy and X-ray diffraction analysis.

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Steroidal esters of the aromatic nitrogen mustard 2-[4-N,N-bis(2-chloroethyl)amino-phenyl]butanoic acid (2-PHE-BU)

Cited by 12 publications

References 32 publications

Synthesis and cytotoxicity of pentacyclic triterpenes‐aniline nitrogen mustard derivatives

Synthesis and cytotoxicity of pentacyclic triterpenes‐aniline nitrogen mustard derivatives

A Pt(IV) Prodrug Combining Chlorambucil and Cisplatin: A Dual-Acting Weapon for Targeting DNA in Cancer Cells

β-Aminocarbonates in Regioselective and Ring Expansion Reactions

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