Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol derivatives as α-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies

Bello, Claudia; Cea, Michele; Bello, Maria Giovanna Dal; Garuti, Anna; Rocco, Ilaria; Cirmena, Gabriella; Morán, Eva; Nahimana, Aimable; Duchosal, Michel A.; Fruscione, Floriana; Pronzato, P.; Grossi, Francesco; Patrone, Franco; Ballestrero, Alberto; Dupuis, Marc; Sordat, Bernard; Nencioni, Alessio; Vogel, Pierre

doi:10.1016/j.bmc.2010.03.009

Cited by 23 publications

(11 citation statements)

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“…For general background to pyrrolidine derivatives, see: Bello et al (2010); Pettersson et al (2011). For related structures, see: Abdul Ajees et al (2002); Selvanayagam et al (2005).…”

Section: Related Literaturementioning

confidence: 99%

“…Pyrrolidine derivatives are used as norepinephrine reuptake inhibitors and 5-HT(1A) partial agonists for treating neuropsychiatric disorders including depression and anxiety (Pettersson et al, 2011). These derivatives are used as alphamannosidase inhibitors and with antitumor activities against hematological and solid malignancies (Bello et al, 2010). In view of these importance, we have undertaken the crystal structure determination of the title compound, a pyrrolidine derivative, and the results are presented here.…”

Section: S1 Commentmentioning

confidence: 99%

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1′-Methyl-4′-(1-naphthyl)-1′′,2′′,3′′,4′′-tetrahydroindane-2-spiro-2′-pyrrolidine-3′-spiro-2′′-naphthalene-1,3,1′′-trione

et al. 2011

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In the title compound, C32H25NO3, the pyrrolidine ring adopts an envelope conformation, whereas the cyclohexanone ring in the tetrahydronaphthalene fused-ring system adopts a half-chair conformation. The indanedione unit is oriented at an angle of 58.9 (1)° with respect to the naphthyl ring system. Three intramolecular C—H⋯O close contacts and an intramolecular C—H⋯π interaction are observed. In the crystal, molecules associate via C—H⋯O hydrogen bonds, forming a helical chain with a C(10) motif along the b axis.

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“…For general background to pyrrolidine derivatives, see: Bello et al (2010); Pettersson et al (2011). For related structures, see: Abdul Ajees et al (2002); Selvanayagam et al (2005).…”

Section: Related Literaturementioning

confidence: 99%

Section: S1 Commentmentioning

confidence: 99%

1′-Methyl-4′-(1-naphthyl)-1′′,2′′,3′′,4′′-tetrahydroindane-2-spiro-2′-pyrrolidine-3′-spiro-2′′-naphthalene-1,3,1′′-trione

et al. 2011

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“…Pyrrolidine and oxopyrrolidine moieties (figure 1) have served as basic structural motifs for the syntheses of many organic compounds with interesting biological properties. Exciting anticancer activities of heterocyclic compounds embedded with pyrrolidine and oxopyrrolidine units have been reported [6][7][8]. Ambaye et al [9] reported that (R,S)3-{N,N-[bis-(2-chloroethyl)]-amino}-1-(2′-methoxyphenyl)-pyrrolidine-2,5-dione hydrochloride (I) (figure 2) showed antitumor activity against P388 (Menogaril-resistant mouse leukemia) and L1210 (mouse lymphocytic leukemia) cell lines; its co-administration with methotrexate resulted in significant increase of activity against these cancers.…”

Section: Introductionmentioning

confidence: 99%

Copper(II), nickel(II), and ruthenium(III) complexes of an oxopyrrolidine-based heterocyclic ligand as anticancer agents

Wani

ALOthman

Ali

et al. 2014

Journal of Coordination Chemistry

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An oxopyrrolidine-based ligand [3-(4-chlorobenzylidine)-5-(5-amino-1,3,4-thiadiazol-2-yl)pyrrolidin-2-one] was synthesized by coupling pyroglutamic acid with p-chlorobenzaldehyde followed by cyclization with thiosemicarbazide in presence of oxyphosphoryl chloride. Copper, nickel, and ruthenium complexes of the ligand were also synthesized. The electrolytic nature, with octahedral geometries for nickel and ruthenium complexes, was observed, while tetragonally distorted octahedral geometry for copper complex was proposed. The complexes were resistant to dissociation and degradation in 5% DMSO solutions of PBS (pH 7.4). DNA binding constants (K b ) for ligand, copper, nickel, and ruthenium complexes were 1.15 × 10 5 , 1.67 × 10 5 , 1.87 × 10 5 , and 1.007 × 10 6 M −1 , respectively, indicating quite strong binding with DNA. In silico studies also showed that the ligand interacted with DNA mainly through van der Waal's forces. The docking energy of ligand−DNA adduct was -30.45 kJ M -1 , suggesting a good affinity of the reported ligand with DNA. Both the ligand and its complexes were less toxic to RBCs as compared to doxorubicin. All the compounds showed moderate anticancer activities on MCF-7 (wild type) breast cancer cell lines.

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“…These derivatives are also used as -mannosidase inhibitors and have antitumor activities against hematological and solid malignancies (Bello et al, 2010). In view of their importance, we have undertaken the synthesis and crystal structure determination of the title compound and the results are presented herein.…”

Section: Structure Descriptionmentioning

confidence: 99%

1-Allyl-3′-phenyl-6′H-spiro[indoline-3,4′-isoxazolo[4′,5′:5,6]pyrido[2,3-d]pyrimidine]-2,5′,7′(8′H,9′H)-trione dimethyl sulfoxide monosolvate

Seethalakshmi

Palanivel²

2017

IUCr Data

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In the title solvated compound, C 24 H 17 N 5 O 4 ÁC 2 H 6 OS, the solvent molecule, dimethyl sulfoxide, is linked to the title molecule by an N-HÁ Á ÁO hydrogen bond. The pyridine ring adopts a twist-boat conformation. The isoxazole ring is inclined to the indoline ring system, the pyrimidine ring, and the phenyl ring by 82.31 (7), 10.41 (8) and 53.77 (10) , respectively. There is an intramolecular C-HÁ Á Á interaction present involving the phenyl ring and the indoline ring system. In the crystal, molecules are connected by two pairs of N-HÁ Á ÁO hydrogen bonds, forming chains along the b-axis direction, and enclosing R 2 2 (8) and R 2 2 (14) ring motifs. The chains are linked by C-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonds and offset -interactions, between the pyrimidine and isoxazole rings of inversion-related molecules [centroid-centroid distance = 3.7140 (9) Å ], forming a three-dimensional structure. Structure descriptionPyrrolidine derivatives are used as norepinephrine reuptake inhibitors and 5-HT(1A) partial agonists for treating neuropsychiatric disorders including depression and anxiety (Pettersson et al., 2011). These derivatives are also used as -mannosidase inhibitors and have antitumor activities against hematological and solid malignancies (Bello et al., 2010). In view of their importance, we have undertaken the synthesis and crystal structure determination of the title compound and the results are presented herein.The molecular structure of the title compound is illustrated in Fig. 1. The solvent molecule is attached to the title molecule via an N4-H4AÁ Á ÁO5 hydrogen bond and there is an intramolecular C-HÁ Á Á interaction present involving the phenyl ring (C1-C6) and the indoline (N5/C13/C15-C21) ring system ( Fig. 1 and Table 1). The sum of the

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Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol derivatives as α-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies

Cited by 23 publications

References 56 publications

1′-Methyl-4′-(1-naphthyl)-1′′,2′′,3′′,4′′-tetrahydroindane-2-spiro-2′-pyrrolidine-3′-spiro-2′′-naphthalene-1,3,1′′-trione

1′-Methyl-4′-(1-naphthyl)-1′′,2′′,3′′,4′′-tetrahydroindane-2-spiro-2′-pyrrolidine-3′-spiro-2′′-naphthalene-1,3,1′′-trione

Copper(II), nickel(II), and ruthenium(III) complexes of an oxopyrrolidine-based heterocyclic ligand as anticancer agents

1-Allyl-3′-phenyl-6′H-spiro[indoline-3,4′-isoxazolo[4′,5′:5,6]pyrido[2,3-d]pyrimidine]-2,5′,7′(8′H,9′H)-trione dimethyl sulfoxide monosolvate

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