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1-Benzylpyrrolidine-2,5-dicarboxylic acid diethyl ester - CAS 93478-48-9

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Category
Main Product
Product Name
1-Benzylpyrrolidine-2,5-dicarboxylic acid diethyl ester
Catalog Number
93478-48-9
CAS Number
93478-48-9
Molecular Weight
305.37
Molecular Formula
C17H23NO4
COA
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MSDS
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Structure
CAS 93478-48-9 1-Benzylpyrrolidine-2,5-dicarboxylic acid diethyl ester
Specification
Purity
95%
Reference Reading
1.Leishmania donovani: a glycosyl dihydropyridine analogue induces apoptosis like cell death via targeting pteridine reductase 1 in promastigotes.
Kaur J1, Singh BK, Tripathi RP, Singh P, Singh N. Exp Parasitol. 2009 Nov;123(3):258-64. doi: 10.1016/j.exppara.2009.07.009. Epub 2009 Aug 6.
Targeting of pteridine reductase 1 (PTR1) in Leishmania is essential for development of successful antifolate chemotherapy. In search for specific inhibitors of PTR1 we have previously reported phenyl 1,4-dihydropyridine ring as the lead structure showing antileishmanial efficacy in vitro and by the oral route in vivo. In this study, we present programmed cell death inducing potential of this glycosyl dihydropyridine analogue (2,6-dimethyl-4-(3-O-benzyl-1,2-O-isopropylidene-beta-l-threo-pentofuranos-4-yl)-1-phenyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester). Flow cytometric analysis revealed that this analogue induces cell cycle arrest at G2/M phase with subsequent increase in sub-G1 peak. Incubation of Leishmania promastigotes with this analogue causes exposure of phosphatidylserine to the outer leaflet of plasma membrane, formation of reactive oxygen species, depolarization of mitochondrial membrane potential and concomitant nuclear alterations that included DNA fragmentation.
2.Anti-inflammatory and immunosuppressive activities of 1,3-dicyclopentyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylic acid diethyl ester (ZL-5015).
Lun Y1, Xia H, Zhang Q, Yu C, Chen N, Li X, Liu S, Lei L. Int Immunopharmacol. 2013 Oct;17(2):168-77. doi: 10.1016/j.intimp.2013.05.032. Epub 2013 Jun 19.
The aim of this study is to investigate the anti-inflammatory and immunosuppressive effects of ZL-5015 (1,3-dicyclopentyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylic acid diethyl ester) in order to determine its potential as a lead compound to develop novel drugs with both anti-inflammatory and immunosuppressive activities. Inflammatory in vivo models (specifically, acetic acid-induced mouse writhing, xylene-induced mouse ear swelling and carrageenan-induced rat paw edema) and in vitro models (specifically, lipopolysaccharide (LPS)-induced production of nitric oxide (NO), prostaglandin E2 (PGE2), tumor necrosis factor α (TNF-α) and interleukin 10 (IL-10) by mouse peritoneal macrophages and RAW264.7 cells) were used to evaluate the anti-inflammatory activities. Immunological in vivo models (specifically, rabbit red blood cells (RRBC)-induced mouse hemolysin production, 2,4-dinitrofluorobenzene (DNFB)-induced delayed type hypersensitivity (DTH) and adjuvant-induced rat arthritis) and in vitro models (specifically, concanavalin A (Con A) and LPS-stimulated mouse splenocyte proliferation) were applied to estimate the immunosuppressive effects.
3.Antihypertensive and antiarrhythmic properties of a para-hydroxy[bis(ortho-morpholinylmethyl)]phenyl-1,4-DHP compound: comparison with other compounds of the same kind and relationship with logP values.
Abrego VH1, Martínez-Pérez B, Torres LA, Angeles E, Martínez L, Marroquín-Pascual JL, Moya-Hernández R, Amaro-Recillas HA, Rueda-Jackson JC, Rodríguez-Barrientos D, Rojas-Hernández A. Eur J Med Chem. 2010 Oct;45(10):4622-30. doi: 10.1016/j.ejmech.2010.07.027. Epub 2010 Jul 23.
A new para-hydroxy[bis(ortho-morpholinylmethyl)]phenyl-1,4-DHP substituted compound, (4-(4-hydroxy-3,5-bis(morpholin-4-ylmethyl)phenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester, LQM300), with antihypertensive and antiarrhythmic properties, has been synthesized. Four pKa values of this compound have been determined with the aid of the program SQUAD, at pseudo-physiological conditions (T = 37 degrees C and I = 0.15 M) by UV spectrophotometry and at T = 25 degrees C and I = 0.05 M by Capillary Zone Electrophoresis (CZE). The logP = 2.7 +/- 0.2 between n-octanol and water, has been estimated by UV spectrophotometry. The antihypertensive and antiarrhythmic efficacies as well as the logP values have been compared with other compounds of the same kind and related with their structure.
4.Leishmania donovani: oral therapy with glycosyl 1,4-dihydropyridine analogue showing apoptosis like phenotypes targeting pteridine reductase 1 in intracellular amastigotes.
Kaur J1, Singh N, Singh BK, Dube A, Tripathi RP, Singh P, Singh N. Exp Parasitol. 2010 Jul;125(3):310-4. doi: 10.1016/j.exppara.2010.02.011. Epub 2010 Feb 26.
Glycosyl 1,4-dihydropyridine analogue (2,6-dimethyl-4-(3-O-benzyl-1,2-O-isopropylidene-beta-l-threo pentofuranos-4-yl)-1-phenyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester) synthesized in our laboratory, inhibited Leishmania donovani infection in vitro and in hamsters (Mesocricetus auratus) when administered orally. This analogue is nontoxic, cell-permeable and orally effective. This glycosyl dihydropyridine analogue functioned through arrest of cells in sub-G0/G1-phase, triggering mitochondrial membrane depolarization-mediated programmed cell death of the intracellular amastigotes.
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