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(1R,2S)-Benzyl N-[3-(diisopropylaminocarbonyl)-2-phenylprop-3-enyl]carbamate.

Acta crystallographica. Section E, Structure reports online

Qu H, Carducci MD, Nichol GS, Hruby VJ.
PMID: 17710225
Acta Crystallogr Sect E Struct Rep Online. 2006 Sep;62(9):o3921-o3922. doi: 10.1107/S1600536806032041.

The title compound, C(25)H(32)N(2)O(3), was synthesized as part of a series of related compounds using a modified Eschenmoser-Claisen rearrangement reaction. The compound is racemic and the structure features a centrosymmetric hydrogen-bonded dimerization along with some aromatic stacking stabilization.

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Qu H, Carducci MD, Nichol GS, et al. (1R,2S)-Benzyl N-[3-(diisopropylaminocarbonyl)-2-phenylprop-3-enyl]carbamate. Acta Crystallogr Sect E Struct Rep Online. 2006;62(9):o3921-o3922doi: 10.1107/S1600536806032041.
Qu, H., Carducci, M. D., Nichol, G. S., & Hruby, V. J. (2006). (1R,2S)-Benzyl N-[3-(diisopropylaminocarbonyl)-2-phenylprop-3-enyl]carbamate. Acta crystallographica. Section E, Structure reports online, 62(9), o3921-o3922. https://doi.org/10.1107/S1600536806032041
Qu, Hongchang, et al. "(1R,2S)-Benzyl N-[3-(diisopropylaminocarbonyl)-2-phenylprop-3-enyl]carbamate." Acta crystallographica. Section E, Structure reports online vol. 62,9 (2006): o3921-o3922. doi: https://doi.org/10.1107/S1600536806032041
Qu H, Carducci MD, Nichol GS, Hruby VJ. (1R,2S)-Benzyl N-[3-(diisopropylaminocarbonyl)-2-phenylprop-3-enyl]carbamate. Acta Crystallogr Sect E Struct Rep Online. 2006 Sep;62(9):o3921-o3922. doi: 10.1107/S1600536806032041. PMID: 17710225; PMCID: PMC1950127.
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Multivalent Interactions: Synthesis and Evaluation of Melanotropin Multimers - Tools for Melanoma Targeting.

ACS medicinal chemistry letters

Brabez N, Saunders K, Nguyen KL, Jayasundera TB, Weber C, Lynch RM, Chassaing G, Lavielle S, Hruby VJ.
PMID: 23524643
ACS Med Chem Lett. 2013 Jan 01;4(1):98-102. doi: 10.1021/ml300312b. Epub 2012 Nov 24.

In order to develop agents for early detection and selective treatment of melanomas, high affinity and high specificity molecular tools are required. Enhanced specificity may be obtained by simultaneously binding to multiple cell surface targets

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Brabez N, Saunders K, Nguyen KL, et al. Multivalent Interactions: Synthesis and Evaluation of Melanotropin Multimers - Tools for Melanoma Targeting. ACS Med Chem Lett. 2012;4(1):98-102doi: 10.1021/ml300312b.
Brabez, N., Saunders, K., Nguyen, K. L., Jayasundera, T. B., Weber, C., Lynch, R. M., Chassaing, G., Lavielle, S., & Hruby, V. J. (2013). Multivalent Interactions: Synthesis and Evaluation of Melanotropin Multimers - Tools for Melanoma Targeting. ACS medicinal chemistry letters, 4(1), 98-102. https://doi.org/10.1021/ml300312b
Brabez, Nabila, et al. "Multivalent Interactions: Synthesis and Evaluation of Melanotropin Multimers - Tools for Melanoma Targeting." ACS medicinal chemistry letters vol. 4,1 (2013): 98-102. doi: https://doi.org/10.1021/ml300312b
Brabez N, Saunders K, Nguyen KL, Jayasundera TB, Weber C, Lynch RM, Chassaing G, Lavielle S, Hruby VJ. Multivalent Interactions: Synthesis and Evaluation of Melanotropin Multimers - Tools for Melanoma Targeting. ACS Med Chem Lett. 2013 Jan 01;4(1):98-102. doi: 10.1021/ml300312b. Epub 2012 Nov 24. PMID: 23524643; PMCID: PMC3601667.
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Isomerization/Recyclization of some 5-Ethoxycarbonyl-pyrimidines.

Journal of heterocyclic chemistry

Vardanyan RS, Hruby VJ, Danagulyan GG, Mkrtchyan AD.
PMID: 16467919
J Heterocycl Chem. 2005;42(4):557-562. doi: 10.1002/jhet.5570420413.

This communication reports on the investigation of a new recyclization conversion of a pyrimidine ring, which can be referred to as C-C recyclization. In this reaction the nucleophile cleaves the pyrimidine ring at the N(3)-C(4) bond, and following rotation...

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Vardanyan RS, Hruby VJ, Danagulyan GG, et al. Isomerization/Recyclization of some 5-Ethoxycarbonyl-pyrimidines. J Heterocycl Chem. 2005;42(4):557-562doi: 10.1002/jhet.5570420413.
Vardanyan, R. S., Hruby, V. J., Danagulyan, G. G., & Mkrtchyan, A. D. (2005). Isomerization/Recyclization of some 5-Ethoxycarbonyl-pyrimidines. Journal of heterocyclic chemistry, 42(4), 557-562. https://doi.org/10.1002/jhet.5570420413
Vardanyan, R S, et al. "Isomerization/Recyclization of some 5-Ethoxycarbonyl-pyrimidines." Journal of heterocyclic chemistry vol. 42,4 (2005): 557-562. doi: https://doi.org/10.1002/jhet.5570420413
Vardanyan RS, Hruby VJ, Danagulyan GG, Mkrtchyan AD. Isomerization/Recyclization of some 5-Ethoxycarbonyl-pyrimidines. J Heterocycl Chem. 2005;42(4):557-562. doi: 10.1002/jhet.5570420413. PMID: 16467919; PMCID: PMC1351139.
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Proton sharing and transfer in some zwitterionic compounds based on 4-oxo-4-((1-phenethylpiperidin-4-yl)(phenyl)amino)alcanoic acids.

CrystEngComm

Nichol GS, Kumirov VK, Vardanyan R, Hruby VJ.
PMID: 25425961
CrystEngComm. 2010;12(11):3651-3657. doi: 10.1039/B923698H.

Three compounds, each derived from Fentanyl and differing essentially only in the length of a carboxylic acid chain, were synthesized and yielded four crystal structures three of which share several structural similarities, including the length of the chain, while...

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Nichol GS, Kumirov VK, Vardanyan R, et al. Proton sharing and transfer in some zwitterionic compounds based on 4-oxo-4-((1-phenethylpiperidin-4-yl)(phenyl)amino)alcanoic acids. CrystEngComm. 2010;12(11):3651-3657doi: 10.1039/B923698H.
Nichol, G. S., Kumirov, V. K., Vardanyan, R., & Hruby, V. J. (2010). Proton sharing and transfer in some zwitterionic compounds based on 4-oxo-4-((1-phenethylpiperidin-4-yl)(phenyl)amino)alcanoic acids. CrystEngComm, 12(11), 3651-3657. https://doi.org/10.1039/B923698H
Nichol, Gary S, et al. "Proton sharing and transfer in some zwitterionic compounds based on 4-oxo-4-((1-phenethylpiperidin-4-yl)(phenyl)amino)alcanoic acids." CrystEngComm vol. 12,11 (2010): 3651-3657. doi: https://doi.org/10.1039/B923698H
Nichol GS, Kumirov VK, Vardanyan R, Hruby VJ. Proton sharing and transfer in some zwitterionic compounds based on 4-oxo-4-((1-phenethylpiperidin-4-yl)(phenyl)amino)alcanoic acids. CrystEngComm. 2010;12(11):3651-3657. doi: 10.1039/B923698H. PMID: 25425961; PMCID: PMC4241297.
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[N-({(R)-2-[(N-Benzylprolyl)amino]phenyl}-phenylmethylene)-2(S)-(pent-4-enyl)-glycinato]nickel(II).

Acta crystallographica. Section E, Structure reports online

Carducci MD, Gu X, Cole JR, Hruby VJ.
PMID: 17268578
Acta Crystallogr Sect E Struct Rep Online. 2006 Jun;62(6):m1219-m1220. doi: 10.1107/S160053680601244X.

The title compound, [Ni(C(32)H(33)N(3)O(3))], crystallized as a minor product during the purification of its 2(R)-pent-4-enyl diastereomer. Mixtures of the title compound and its enantiomer self-resolve.

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Carducci MD, Gu X, Cole JR, et al. [N-({(R)-2-[(N-Benzylprolyl)amino]phenyl}-phenylmethylene)-2(S)-(pent-4-enyl)-glycinato]nickel(II). Acta Crystallogr Sect E Struct Rep Online. 2006;62(6):m1219-m1220doi: 10.1107/S160053680601244X.
Carducci, M. D., Gu, X., Cole, J. R., & Hruby, V. J. (2006). [N-({(R)-2-[(N-Benzylprolyl)amino]phenyl}-phenylmethylene)-2(S)-(pent-4-enyl)-glycinato]nickel(II). Acta crystallographica. Section E, Structure reports online, 62(6), m1219-m1220. https://doi.org/10.1107/S160053680601244X
Carducci, Michael D, et al. "[N-({(R)-2-[(N-Benzylprolyl)amino]phenyl}-phenylmethylene)-2(S)-(pent-4-enyl)-glycinato]nickel(II)." Acta crystallographica. Section E, Structure reports online vol. 62,6 (2006): m1219-m1220. doi: https://doi.org/10.1107/S160053680601244X
Carducci MD, Gu X, Cole JR, Hruby VJ. [N-({(R)-2-[(N-Benzylprolyl)amino]phenyl}-phenylmethylene)-2(S)-(pent-4-enyl)-glycinato]nickel(II). Acta Crystallogr Sect E Struct Rep Online. 2006 Jun;62(6):m1219-m1220. doi: 10.1107/S160053680601244X. PMID: 17268578; PMCID: PMC1785113.
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High throughput synthesis of peptides and peptidomimetics.

Chimica oggi

Hruby VJ, Vagner J.
PMID: 18618009
Chim Oggi. 2006;24(4):18-21.

Peptide synthesis has been developed into one of the most efficient synthetic procedures in organic chemistry. The problems of orthogonal functional group protection and amide bond formation without racemization have been developed in a number of ingenious strategies. Optimization,...

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Hruby VJ, Vagner J. High throughput synthesis of peptides and peptidomimetics. Chim Oggi. 2006;24(4):18-21
Hruby, V. J., & Vagner, J. (2006). High throughput synthesis of peptides and peptidomimetics. Chimica oggi, 24(4), 18-21.
Hruby, Victor J, and Vagner, Josef. "High throughput synthesis of peptides and peptidomimetics." Chimica oggi vol. 24,4 (2006): 18-21.
Hruby VJ, Vagner J. High throughput synthesis of peptides and peptidomimetics. Chim Oggi. 2006;24(4):18-21. PMID: 18618009; PMCID: PMC2447911.
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Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic.

Tetrahedron letters

Min BJ, Gu X, Yamamoto T, Petrov RR, Qu H, Lee YS, Hruby VJ.
PMID: 19340283
Tetrahedron Lett. 2008 Mar 31;49(14):2316-2319. doi: 10.1016/j.tetlet.2008.01.137.

A substituted hydropyrazino[1,2-a]pyrimidin-6-one derivative was synthesized stereoselectively via the intramolecular N-acyliminium ion cyclization between an amide nitrogen and an N(α)-acetal derived from Cbz-protected aminopropyl-phenylalaninamide in very good yields. The formation of a single diastereomer is due to the low...

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Min BJ, Gu X, Yamamoto T, et al. Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic. Tetrahedron Lett. 2008;49(14):2316-2319doi: 10.1016/j.tetlet.2008.01.137.
Min, B. J., Gu, X., Yamamoto, T., Petrov, R. R., Qu, H., Lee, Y. S., & Hruby, V. J. (2008). Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic. Tetrahedron letters, 49(14), 2316-2319. https://doi.org/10.1016/j.tetlet.2008.01.137
Min, Byoung J, et al. "Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic." Tetrahedron letters vol. 49,14 (2008): 2316-2319. doi: https://doi.org/10.1016/j.tetlet.2008.01.137
Min BJ, Gu X, Yamamoto T, Petrov RR, Qu H, Lee YS, Hruby VJ. Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic. Tetrahedron Lett. 2008 Mar 31;49(14):2316-2319. doi: 10.1016/j.tetlet.2008.01.137. PMID: 19340283; PMCID: PMC2390882.
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Synthesis and Crystallographic Study of .

Journal of chemical crystallography

Nichol GS, Vardanyan R, Hruby VJ.
PMID: 25505832
J Chem Crystallogr. 2010 Nov;40(11):961-964. doi: 10.1007/s10870-010-9771-1.

As part of a study into new Fentanyl-derived opioid compounds with potent analgesic activity and reduced side effects the starting material title compound, C

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Nichol GS, Vardanyan R, Hruby VJ. Synthesis and Crystallographic Study of . J Chem Crystallogr. 2010;40(11):961-964doi: 10.1007/s10870-010-9771-1.
Nichol, G. S., Vardanyan, R., & Hruby, V. J. (2010). Synthesis and Crystallographic Study of . Journal of chemical crystallography, 40(11), 961-964. https://doi.org/10.1007/s10870-010-9771-1
Nichol, Gary S, et al. "Synthesis and Crystallographic Study of ." Journal of chemical crystallography vol. 40,11 (2010): 961-964. doi: https://doi.org/10.1007/s10870-010-9771-1
Nichol GS, Vardanyan R, Hruby VJ. Synthesis and Crystallographic Study of . J Chem Crystallogr. 2010 Nov;40(11):961-964. doi: 10.1007/s10870-010-9771-1. PMID: 25505832; PMCID: PMC4260262.
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Recyclization reactions of 1-alkylpyrimidinium salts.

Heterocyclic communications

Vardanyan RS, Danagulyan GG, Mkrtchyan AD, Hruby VJ.
PMID: 25400328
Heterocycl Comm. 2011 Sep;17(3):129-133. doi: 10.1515/hc.2011.025.

The reaction of 4-amino-2-benzyl-1-methyl-5-ethoxycarbonylpyrimidinium iodide (

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Vardanyan RS, Danagulyan GG, Mkrtchyan AD, et al. Recyclization reactions of 1-alkylpyrimidinium salts. Heterocycl Comm. 2011;17(3):129-133doi: 10.1515/hc.2011.025.
Vardanyan, R. S., Danagulyan, G. G., Mkrtchyan, A. D., & Hruby, V. J. (2011). Recyclization reactions of 1-alkylpyrimidinium salts. Heterocyclic communications, 17(3), 129-133. https://doi.org/10.1515/hc.2011.025
Vardanyan, Ruben S, et al. "Recyclization reactions of 1-alkylpyrimidinium salts." Heterocyclic communications vol. 17,3 (2011): 129-133. doi: https://doi.org/10.1515/hc.2011.025
Vardanyan RS, Danagulyan GG, Mkrtchyan AD, Hruby VJ. Recyclization reactions of 1-alkylpyrimidinium salts. Heterocycl Comm. 2011 Sep;17(3):129-133. doi: 10.1515/hc.2011.025. PMID: 25400328; PMCID: PMC4230491.
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4-{N-[2-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionyl]anilino}-1-phenethylpiperidinium chloride methanol disolvate.

Acta crystallographica. Section E, Structure reports online

Petrov RR, Vardanyan RS, Nichol GS, Carducci MD, Ma SW, Lai JY, Hruby VJ.
PMID: 17268579
Acta Crystallogr Sect E Struct Rep Online. 2006 Jul;62(7):o2815-o2816. doi: 10.1107/S1600536806021817.

The structure of the title compound, a fentanyl derivative with formula C(36)H(36)N(3)O(3) (+)·Cl(-)·2CH(3)OH, crystallizes as a racemic mixture. The organic cation has an extended conformation and the structure displays O-H⋯O, O-H⋯Cl and N-H⋯Cl hydrogen bonding.

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Petrov RR, Vardanyan RS, Nichol GS, et al. 4-{N-[2-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionyl]anilino}-1-phenethylpiperidinium chloride methanol disolvate. Acta Crystallogr Sect E Struct Rep Online. 2006;62(7):o2815-o2816doi: 10.1107/S1600536806021817.
Petrov, R. R., Vardanyan, R. S., Nichol, G. S., Carducci, M. D., Ma, S. W., Lai, J. Y., & Hruby, V. J. (2006). 4-{N-[2-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionyl]anilino}-1-phenethylpiperidinium chloride methanol disolvate. Acta crystallographica. Section E, Structure reports online, 62(7), o2815-o2816. https://doi.org/10.1107/S1600536806021817
Petrov, Ravil R, et al. "4-{N-[2-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionyl]anilino}-1-phenethylpiperidinium chloride methanol disolvate." Acta crystallographica. Section E, Structure reports online vol. 62,7 (2006): o2815-o2816. doi: https://doi.org/10.1107/S1600536806021817
Petrov RR, Vardanyan RS, Nichol GS, Carducci MD, Ma SW, Lai JY, Hruby VJ. 4-{N-[2-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionyl]anilino}-1-phenethylpiperidinium chloride methanol disolvate. Acta Crystallogr Sect E Struct Rep Online. 2006 Jul;62(7):o2815-o2816. doi: 10.1107/S1600536806021817. PMID: 17268579; PMCID: PMC1785114.
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Chiral Effect of a Phe Residue in Position 3 of the Dmt.

ACS medicinal chemistry letters

Lee YS, Qu HC, Davis P, Ma SW, Vardanyan R, Lai J, Porreca F, Hruby VJ.
PMID: 24648867
ACS Med Chem Lett. 2013 Jul 11;4(7):656-659. doi: 10.1021/ml400115n.

In this letter, we describe a structure-activity relationships study, specifically related to the chirality of third amino acid residue in our H-Dmt-L(or D)-Tic analogues, of which C-terminus is attached to a piperidinyl moiety. Observed selectivities and functional activities of...

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Lee YS, Qu HC, Davis P, et al. Chiral Effect of a Phe Residue in Position 3 of the Dmt. ACS Med Chem Lett. 2013;4(7):656-659doi: 10.1021/ml400115n.
Lee, Y. S., Qu, H. C., Davis, P., Ma, S. W., Vardanyan, R., Lai, J., Porreca, F., & Hruby, V. J. (2013). Chiral Effect of a Phe Residue in Position 3 of the Dmt. ACS medicinal chemistry letters, 4(7), 656-659. https://doi.org/10.1021/ml400115n
Lee, Yeon Sun, et al. "Chiral Effect of a Phe Residue in Position 3 of the Dmt." ACS medicinal chemistry letters vol. 4,7 (2013): 656-659. doi: https://doi.org/10.1021/ml400115n
Lee YS, Qu HC, Davis P, Ma SW, Vardanyan R, Lai J, Porreca F, Hruby VJ. Chiral Effect of a Phe Residue in Position 3 of the Dmt. ACS Med Chem Lett. 2013 Jul 11;4(7):656-659. doi: 10.1021/ml400115n. PMID: 24648867; PMCID: PMC3956057.
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tert-Butyl 4-(3,4-dichloro-anilino)piperidine-1-carboxyl-ate.

Acta crystallographica. Section E, Structure reports online

Mehr-Un-Nisa, Munawar MA, Hall GB, Roberts SA, Hruby VJ.
PMID: 23424488
Acta Crystallogr Sect E Struct Rep Online. 2013 Feb 01;69:o205. doi: 10.1107/S1600536812051896. Epub 2013 Jan 09.

In the title compound, C(16)H(22)Cl(2)N(2)O(2), the substituted piperidine ring adopts a chair conformation with both substituents in equatorial positions. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds connect mol-ecules into ribbons along the a-axis direction.

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Mehr-Un-Nisa, Munawar MA, Hall GB, et al. tert-Butyl 4-(3,4-dichloro-anilino)piperidine-1-carboxyl-ate. Acta Crystallogr Sect E Struct Rep Online. 2013;69:o205doi: 10.1107/S1600536812051896.
Mehr-Un-Nisa, Munawar, M. A., Hall, G. B., Roberts, S. A., & Hruby, V. J. (2013). tert-Butyl 4-(3,4-dichloro-anilino)piperidine-1-carboxyl-ate. Acta crystallographica. Section E, Structure reports online, 69o205. https://doi.org/10.1107/S1600536812051896
Mehr-Un-Nisa, et al. "tert-Butyl 4-(3,4-dichloro-anilino)piperidine-1-carboxyl-ate." Acta crystallographica. Section E, Structure reports online vol. 69 (2013): o205. doi: https://doi.org/10.1107/S1600536812051896
Mehr-Un-Nisa, Munawar MA, Hall GB, Roberts SA, Hruby VJ. tert-Butyl 4-(3,4-dichloro-anilino)piperidine-1-carboxyl-ate. Acta Crystallogr Sect E Struct Rep Online. 2013 Feb 01;69:o205. doi: 10.1107/S1600536812051896. Epub 2013 Jan 09. PMID: 23424488; PMCID: PMC3569265.
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Showing 1 to 12 of 15 entries