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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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C-terminal modified Enkephalin-like tetrapeptides with enhanced affinities at the kappa opioid receptor and monoamine transporters.

Bioorganic & medicinal chemistry

Mehr-Un-Nisa, Munawar MA, Rankin D, Hruby VJ, Porreca F, Lee YS.
PMID: 34798381
Bioorg Med Chem. 2021 Dec 01;51:116509. doi: 10.1016/j.bmc.2021.116509. Epub 2021 Nov 11.

A new series of enkephalin-like tetrapeptide analogs modified at the C-terminus by an N-(3,4-dichlorophenyl)-N-(piperidin-4-yl)propionamide (DPP) moiety were designed, synthesized, and tested for their binding affinities at opioid receptors and monoamine transporters to evaluate their potential multifunctional activity for the...

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Mehr-Un-Nisa, Munawar MA, Rankin D, et al. C-terminal modified Enkephalin-like tetrapeptides with enhanced affinities at the kappa opioid receptor and monoamine transporters. Bioorg Med Chem. 2021;51:116509doi: 10.1016/j.bmc.2021.116509.
Mehr-Un-Nisa, Munawar, M. A., Rankin, D., Hruby, V. J., Porreca, F., & Lee, Y. S. (2021). C-terminal modified Enkephalin-like tetrapeptides with enhanced affinities at the kappa opioid receptor and monoamine transporters. Bioorganic & medicinal chemistry, 51116509. https://doi.org/10.1016/j.bmc.2021.116509
Mehr-Un-Nisa, et al. "C-terminal modified Enkephalin-like tetrapeptides with enhanced affinities at the kappa opioid receptor and monoamine transporters." Bioorganic & medicinal chemistry vol. 51 (2021): 116509. doi: https://doi.org/10.1016/j.bmc.2021.116509
Mehr-Un-Nisa, Munawar MA, Rankin D, Hruby VJ, Porreca F, Lee YS. C-terminal modified Enkephalin-like tetrapeptides with enhanced affinities at the kappa opioid receptor and monoamine transporters. Bioorg Med Chem. 2021 Dec 01;51:116509. doi: 10.1016/j.bmc.2021.116509. Epub 2021 Nov 11. PMID: 34798381; PMCID: PMC8649046.
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Synthesis of constrained analogues of cholecystokinin/opioid chimeric peptides.

Tetrahedron letters

Ndungu JM, Cain JP, Davis P, Ma SW, Vanderah TW, Lai J, Porreca F, Hruby VJ.
PMID: 17203138
Tetrahedron Lett. 2006 Mar 27;47(13):2233-2236. doi: 10.1016/j.tetlet.2006.01.096.

In our ongoing research on the synthesis of constrained analogues of CCK/opioid chimeric peptides, a bicyclic dipeptide mimetic for Nle-Asp was designed and synthesized. Starting from β-allyl substituted aspartic acids, the terminal double bond was oxidized resulting in spontaneous...

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Ndungu JM, Cain JP, Davis P, et al. Synthesis of constrained analogues of cholecystokinin/opioid chimeric peptides. Tetrahedron Lett. 2006;47(13):2233-2236doi: 10.1016/j.tetlet.2006.01.096.
Ndungu, J. M., Cain, J. P., Davis, P., Ma, S. W., Vanderah, T. W., Lai, J., Porreca, F., & Hruby, V. J. (2006). Synthesis of constrained analogues of cholecystokinin/opioid chimeric peptides. Tetrahedron letters, 47(13), 2233-2236. https://doi.org/10.1016/j.tetlet.2006.01.096
Ndungu, John M, et al. "Synthesis of constrained analogues of cholecystokinin/opioid chimeric peptides." Tetrahedron letters vol. 47,13 (2006): 2233-2236. doi: https://doi.org/10.1016/j.tetlet.2006.01.096
Ndungu JM, Cain JP, Davis P, Ma SW, Vanderah TW, Lai J, Porreca F, Hruby VJ. Synthesis of constrained analogues of cholecystokinin/opioid chimeric peptides. Tetrahedron Lett. 2006 Mar 27;47(13):2233-2236. doi: 10.1016/j.tetlet.2006.01.096. PMID: 17203138; PMCID: PMC1761685.
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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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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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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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Blockade of non-opioid excitatory effects of spinal dynorphin A at bradykinin receptors.

Receptors & clinical investigation

Lee YS, Hall SM, Ramos-Colon C, Remesic M, Rankin D, Vanderah TW, Porreca F, Lai J, Hruby VJ.
PMID: 26221618
Receptors Clin Investig. 2015;2(1). doi: 10.14800/rci.517.

Dynorphin A (Dyn A) is an endogenous opioid ligand that possesses neuroinhibitory (antinociceptive) effects via μ, δ, and κ opioid receptors. However, under chronic pain conditions, up-regulated spinal Dyn A can also interact with bradykinin receptors (BRs) to promote...

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Lee YS, Hall SM, Ramos-Colon C, et al. Blockade of non-opioid excitatory effects of spinal dynorphin A at bradykinin receptors. Receptors Clin Investig. 2015;2(1)doi: 10.14800/rci.517.
Lee, Y. S., Hall, S. M., Ramos-Colon, C., Remesic, M., Rankin, D., Vanderah, T. W., Porreca, F., Lai, J., & Hruby, V. J. (2015). Blockade of non-opioid excitatory effects of spinal dynorphin A at bradykinin receptors. Receptors & clinical investigation, 2(1), . https://doi.org/10.14800/rci.517
Lee, Yeon Sun, et al. "Blockade of non-opioid excitatory effects of spinal dynorphin A at bradykinin receptors." Receptors & clinical investigation vol. 2,1 (2015). doi: https://doi.org/10.14800/rci.517
Lee YS, Hall SM, Ramos-Colon C, Remesic M, Rankin D, Vanderah TW, Porreca F, Lai J, Hruby VJ. Blockade of non-opioid excitatory effects of spinal dynorphin A at bradykinin receptors. Receptors Clin Investig. 2015;2(1). doi: 10.14800/rci.517. PMID: 26221618; PMCID: PMC4515361.
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1-(4-Methoxy-phen-yl)-3-phenyl-1H-pyrazol-5-amine.

Acta crystallographica. Section E, Structure reports online

Kumarasinghe IR, Hruby VJ, Nichol GS.
PMID: 21583972
Acta Crystallogr Sect E Struct Rep Online. 2009 Apr 30;65:o1170. doi: 10.1107/S1600536809015463.

The synthesis of the title compound, C(16)H(15)N(3)O, is regiospecific and single-crystal X-ray diffraction provides the only means of unambiguous structural analysis, with the benzene ring bonded to the imine C atom. The phenyl ring and the essentially planar (r.m.s....

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Kumarasinghe IR, Hruby VJ, Nichol GS. 1-(4-Methoxy-phen-yl)-3-phenyl-1H-pyrazol-5-amine. Acta Crystallogr Sect E Struct Rep Online. 2009;65:o1170doi: 10.1107/S1600536809015463.
Kumarasinghe, I. R., Hruby, V. J., & Nichol, G. S. (2009). 1-(4-Methoxy-phen-yl)-3-phenyl-1H-pyrazol-5-amine. Acta crystallographica. Section E, Structure reports online, 65o1170. https://doi.org/10.1107/S1600536809015463
Kumarasinghe, Isuru R, et al. "1-(4-Methoxy-phen-yl)-3-phenyl-1H-pyrazol-5-amine." Acta crystallographica. Section E, Structure reports online vol. 65 (2009): o1170. doi: https://doi.org/10.1107/S1600536809015463
Kumarasinghe IR, Hruby VJ, Nichol GS. 1-(4-Methoxy-phen-yl)-3-phenyl-1H-pyrazol-5-amine. Acta Crystallogr Sect E Struct Rep Online. 2009 Apr 30;65:o1170. doi: 10.1107/S1600536809015463. PMID: 21583972; PMCID: PMC2977835.
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Synthesis and Investigation of Mixed μ-Opioid and δ-Opioid Agonists as Possible Bivalent Ligands for Treatment of Pain.

Journal of heterocyclic chemistry

Vardanyan RS, Cain JP, Haghighi SM, Kumirov VK, McIntosh MI, Sandweiss AJ, Porreca F, Hruby VJ.
PMID: 28819330
J Heterocycl Chem. 2017 Mar;54(2):1228-1235. doi: 10.1002/jhet.2696. Epub 2016 Jun 01.

Several studies have suggested functional association between μ-opioid and δ-opioid receptors and showed that μ-activity could be modulated by δ-ligands. The general conclusion is that agonists for the δ-receptor can enhance the analgesic potency and efficacy of μ-agonists. Our...

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Vardanyan RS, Cain JP, Haghighi SM, et al. Synthesis and Investigation of Mixed μ-Opioid and δ-Opioid Agonists as Possible Bivalent Ligands for Treatment of Pain. J Heterocycl Chem. 2016;54(2):1228-1235doi: 10.1002/jhet.2696.
Vardanyan, R. S., Cain, J. P., Haghighi, S. M., Kumirov, V. K., McIntosh, M. I., Sandweiss, A. J., Porreca, F., & Hruby, V. J. (2017). Synthesis and Investigation of Mixed μ-Opioid and δ-Opioid Agonists as Possible Bivalent Ligands for Treatment of Pain. Journal of heterocyclic chemistry, 54(2), 1228-1235. https://doi.org/10.1002/jhet.2696
Vardanyan, Ruben S, et al. "Synthesis and Investigation of Mixed μ-Opioid and δ-Opioid Agonists as Possible Bivalent Ligands for Treatment of Pain." Journal of heterocyclic chemistry vol. 54,2 (2017): 1228-1235. doi: https://doi.org/10.1002/jhet.2696
Vardanyan RS, Cain JP, Haghighi SM, Kumirov VK, McIntosh MI, Sandweiss AJ, Porreca F, Hruby VJ. Synthesis and Investigation of Mixed μ-Opioid and δ-Opioid Agonists as Possible Bivalent Ligands for Treatment of Pain. J Heterocycl Chem. 2017 Mar;54(2):1228-1235. doi: 10.1002/jhet.2696. Epub 2016 Jun 01. PMID: 28819330; PMCID: PMC5557416.
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C-terminal modified Enkephalin-like tetrapeptides with enhanced affinities at the kappa opioid receptor and monoamine transporters.

Bioorganic & medicinal chemistry

Mehr-Un-Nisa, Munawar MA, Rankin D, Hruby VJ, Porreca F, Lee YS.
PMID: 34798381
Bioorg Med Chem. 2021 Dec 01;51:116509. doi: 10.1016/j.bmc.2021.116509. Epub 2021 Nov 11.

A new series of enkephalin-like tetrapeptide analogs modified at the C-terminus by an N-(3,4-dichlorophenyl)-N-(piperidin-4-yl)propionamide (DPP) moiety were designed, synthesized, and tested for their binding affinities at opioid receptors and monoamine transporters to evaluate their potential multifunctional activity for the...

Cite
Mehr-Un-Nisa, Munawar MA, Rankin D, et al. C-terminal modified Enkephalin-like tetrapeptides with enhanced affinities at the kappa opioid receptor and monoamine transporters. Bioorg Med Chem. 2021;51:116509doi: 10.1016/j.bmc.2021.116509.
Mehr-Un-Nisa, Munawar, M. A., Rankin, D., Hruby, V. J., Porreca, F., & Lee, Y. S. (2021). C-terminal modified Enkephalin-like tetrapeptides with enhanced affinities at the kappa opioid receptor and monoamine transporters. Bioorganic & medicinal chemistry, 51116509. https://doi.org/10.1016/j.bmc.2021.116509
Mehr-Un-Nisa, et al. "C-terminal modified Enkephalin-like tetrapeptides with enhanced affinities at the kappa opioid receptor and monoamine transporters." Bioorganic & medicinal chemistry vol. 51 (2021): 116509. doi: https://doi.org/10.1016/j.bmc.2021.116509
Mehr-Un-Nisa, Munawar MA, Rankin D, Hruby VJ, Porreca F, Lee YS. C-terminal modified Enkephalin-like tetrapeptides with enhanced affinities at the kappa opioid receptor and monoamine transporters. Bioorg Med Chem. 2021 Dec 01;51:116509. doi: 10.1016/j.bmc.2021.116509. Epub 2021 Nov 11. PMID: 34798381; PMCID: PMC8649046.
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Showing 1 to 10 of 10 entries