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Rhodium-Catalyzed Direct Bis-cyanation of Arylimidazo[1,2-α]pyridine via Double C-H Activation.

The Journal of organic chemistry

Zhu X, Shen XJ, Tian ZY, Lu S, Tian LL, Liu WB, Song B, Hao XQ.
PMID: 28581299
J Org Chem. 2017 Jun 16;82(12):6022-6031. doi: 10.1021/acs.joc.6b03036. Epub 2017 Jun 05.

An efficient Cp*Rh(III)-catalyzed selective bis-cyanation of arylimidazo[1,2-α]pyridines with N-cyano-N-phenyl-p-methylbenzenesulfonamide via N-directed ortho double C-H activation has been developed. The reaction proceeds with broad functional group tolerance to furnish various cyanated imidazopyridines in high yields. The current methodology exhibits unique...

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Zhu X, Shen XJ, Tian ZY, et al. Rhodium-Catalyzed Direct Bis-cyanation of Arylimidazo[1,2-α]pyridine via Double C-H Activation. J Org Chem. 2017;82(12):6022-6031doi: 10.1021/acs.joc.6b03036.
Zhu, X., Shen, X. J., Tian, Z. Y., Lu, S., Tian, L. L., Liu, W. B., Song, B., & Hao, X. Q. (2017). Rhodium-Catalyzed Direct Bis-cyanation of Arylimidazo[1,2-α]pyridine via Double C-H Activation. The Journal of organic chemistry, 82(12), 6022-6031. https://doi.org/10.1021/acs.joc.6b03036
Zhu, Xinju, et al. "Rhodium-Catalyzed Direct Bis-cyanation of Arylimidazo[1,2-α]pyridine via Double C-H Activation." The Journal of organic chemistry vol. 82,12 (2017): 6022-6031. doi: https://doi.org/10.1021/acs.joc.6b03036
Zhu X, Shen XJ, Tian ZY, Lu S, Tian LL, Liu WB, Song B, Hao XQ. Rhodium-Catalyzed Direct Bis-cyanation of Arylimidazo[1,2-α]pyridine via Double C-H Activation. J Org Chem. 2017 Jun 16;82(12):6022-6031. doi: 10.1021/acs.joc.6b03036. Epub 2017 Jun 05. PMID: 28581299.
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Zolpidem and triazolam interact differentially with a delay interval on a digit-enter-and-recall task.

Human psychopharmacology

Rush CR, Baker RW.
PMID: 12404585
Hum Psychopharmacol. 2001 Mar;16(2):147-157. doi: 10.1002/hup.240.

Zolpidem (AMBIEN((R))), an imidazopyridine, is now the most commonly prescribed hypnotic in the United States. Zolpidem is neuropharmacologically distinct from benzodiazepine hypnotics in that it binds with low affinity to alpha(5)-containing GABA(A)-receptor subtypes. Despite its unique benzodiazepine-receptor binding profile,...

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Rush CR, Baker RW. Zolpidem and triazolam interact differentially with a delay interval on a digit-enter-and-recall task. Hum Psychopharmacol. 2001;16(2):147-157doi: 10.1002/hup.240.
Rush, C. R., & Baker, R. W. (2001). Zolpidem and triazolam interact differentially with a delay interval on a digit-enter-and-recall task. Human psychopharmacology, 16(2), 147-157. https://doi.org/10.1002/hup.240
Rush, Craig R., and Baker, Robert W.. "Zolpidem and triazolam interact differentially with a delay interval on a digit-enter-and-recall task." Human psychopharmacology vol. 16,2 (2001): 147-157. doi: https://doi.org/10.1002/hup.240
Rush CR, Baker RW. Zolpidem and triazolam interact differentially with a delay interval on a digit-enter-and-recall task. Hum Psychopharmacol. 2001 Mar;16(2):147-157. doi: 10.1002/hup.240. PMID: 12404585.
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8-Bromo-3,4-dihydro-2H-1,3-thia-zino[2,3:2',1']imidazo[5',4'-b]pyridine.

Acta crystallographica. Section E, Structure reports online

Ghacham HB, Rodi YK, Capet F, Essassi el M, Ng SW.
PMID: 21579133
Acta Crystallogr Sect E Struct Rep Online. 2010 Apr 14;66:o1079. doi: 10.1107/S1600536810012778.

The imidazopyridine ring system in the title compound, C(9)H(8)BrN(3)S, is almost planar [r.m.s. deviation of the C and N atoms = 0.007 (1) Å]. The S and methyl-ene C atoms connected to the five-membered ring lie within this plane....

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Ghacham HB, Rodi YK, Capet F, et al. 8-Bromo-3,4-dihydro-2H-1,3-thia-zino[2,3:2',1']imidazo[5',4'-b]pyridine. Acta Crystallogr Sect E Struct Rep Online. 2010;66:o1079doi: 10.1107/S1600536810012778.
Ghacham, H. B., Rodi, Y. K., Capet, F., Essassi, e. l. . M., & Ng, S. W. (2010). 8-Bromo-3,4-dihydro-2H-1,3-thia-zino[2,3:2',1']imidazo[5',4'-b]pyridine. Acta crystallographica. Section E, Structure reports online, 66o1079. https://doi.org/10.1107/S1600536810012778
Ghacham, Hend Bel, et al. "8-Bromo-3,4-dihydro-2H-1,3-thia-zino[2,3:2',1']imidazo[5',4'-b]pyridine." Acta crystallographica. Section E, Structure reports online vol. 66 (2010): o1079. doi: https://doi.org/10.1107/S1600536810012778
Ghacham HB, Rodi YK, Capet F, Essassi el M, Ng SW. 8-Bromo-3,4-dihydro-2H-1,3-thia-zino[2,3:2',1']imidazo[5',4'-b]pyridine. Acta Crystallogr Sect E Struct Rep Online. 2010 Apr 14;66:o1079. doi: 10.1107/S1600536810012778. PMID: 21579133; PMCID: PMC2979025.
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4-Benzyl-6-bromo-2-(4-methoxy-phen-yl)-4H-imidazo[4,5-b]pyridine monohydrate.

Acta crystallographica. Section E, Structure reports online

Ouzidan Y, Kandri Rodi Y, Obbade S, Essassi el M, Ng SW.
PMID: 21580751
Acta Crystallogr Sect E Struct Rep Online. 2010 Mar 27;66:o947. doi: 10.1107/S1600536810010391.

The imidazopyridine fused ring in the title compound, C(20)H(16)BrN(3)O·H(2)O, is coplanar with the aromatic ring at the 2-position [dihedral angle = 5.2 (1)°]. In the five-membered imidazo portion, the C-N bond whose C atom is also connected to the...

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Ouzidan Y, Kandri Rodi Y, Obbade S, et al. 4-Benzyl-6-bromo-2-(4-methoxy-phen-yl)-4H-imidazo[4,5-b]pyridine monohydrate. Acta Crystallogr Sect E Struct Rep Online. 2010;66:o947doi: 10.1107/S1600536810010391.
Ouzidan, Y., Kandri Rodi, Y., Obbade, S., Essassi, e. l. . M., & Ng, S. W. (2010). 4-Benzyl-6-bromo-2-(4-methoxy-phen-yl)-4H-imidazo[4,5-b]pyridine monohydrate. Acta crystallographica. Section E, Structure reports online, 66o947. https://doi.org/10.1107/S1600536810010391
Ouzidan, Y, et al. "4-Benzyl-6-bromo-2-(4-methoxy-phen-yl)-4H-imidazo[4,5-b]pyridine monohydrate." Acta crystallographica. Section E, Structure reports online vol. 66 (2010): o947. doi: https://doi.org/10.1107/S1600536810010391
Ouzidan Y, Kandri Rodi Y, Obbade S, Essassi el M, Ng SW. 4-Benzyl-6-bromo-2-(4-methoxy-phen-yl)-4H-imidazo[4,5-b]pyridine monohydrate. Acta Crystallogr Sect E Struct Rep Online. 2010 Mar 27;66:o947. doi: 10.1107/S1600536810010391. PMID: 21580751; PMCID: PMC2983875.
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1,3-Dibenzyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Acta crystallographica. Section E, Structure reports online

Dahmani S, Kandri Rodi Y, Capet F, Essassi el M, Ng SW.
PMID: 21580599
Acta Crystallogr Sect E Struct Rep Online. 2010 Mar 06;66:o754. doi: 10.1107/S1600536810007713.

The imidazopyridine fused-ring in the title compound, C(20)H(16)BrN(3)O, is planar (r.m.s. deviation = 0.011 Å). The phenyl rings of the benzyl substitutents twist away from the central five-membered ring in opposite directions; the rings are aligned at 61.3 (1)...

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Dahmani S, Kandri Rodi Y, Capet F, et al. 1,3-Dibenzyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one. Acta Crystallogr Sect E Struct Rep Online. 2010;66:o754doi: 10.1107/S1600536810007713.
Dahmani, S., Kandri Rodi, Y., Capet, F., Essassi, e. l. . M., & Ng, S. W. (2010). 1,3-Dibenzyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one. Acta crystallographica. Section E, Structure reports online, 66o754. https://doi.org/10.1107/S1600536810007713
Dahmani, S, et al. "1,3-Dibenzyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one." Acta crystallographica. Section E, Structure reports online vol. 66 (2010): o754. doi: https://doi.org/10.1107/S1600536810007713
Dahmani S, Kandri Rodi Y, Capet F, Essassi el M, Ng SW. 1,3-Dibenzyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one. Acta Crystallogr Sect E Struct Rep Online. 2010 Mar 06;66:o754. doi: 10.1107/S1600536810007713. PMID: 21580599; PMCID: PMC2983860.
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Tuning of excited-state intramolecular proton transfer (ESIPT) fluorescence of imidazo[1,2-a]pyridine in rigid matrices by substitution effect.

The Journal of organic chemistry

Mutai T, Sawatani H, Shida T, Shono H, Araki K.
PMID: 23405828
J Org Chem. 2013 Mar 15;78(6):2482-9. doi: 10.1021/jo302711t. Epub 2013 Feb 13.

2-(2'-Hydroxyphenyl)imidazo[1,2-a]pyridine (HPIP, 1) and its derivatives are synthesized, and their fluorescence properties are studied. Although all the compounds show faint dual emission (Φ ≈ 0.01), which is assigned to the normal and excited-state intramolecular proton transfer (ESIPT) fluorescence in...

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Mutai T, Sawatani H, Shida T, et al. Tuning of excited-state intramolecular proton transfer (ESIPT) fluorescence of imidazo[1,2-a]pyridine in rigid matrices by substitution effect. J Org Chem. 2013;78(6):2482-9doi: 10.1021/jo302711t.
Mutai, T., Sawatani, H., Shida, T., Shono, H., & Araki, K. (2013). Tuning of excited-state intramolecular proton transfer (ESIPT) fluorescence of imidazo[1,2-a]pyridine in rigid matrices by substitution effect. The Journal of organic chemistry, 78(6), 2482-9. https://doi.org/10.1021/jo302711t
Mutai, Toshiki, et al. "Tuning of excited-state intramolecular proton transfer (ESIPT) fluorescence of imidazo[1,2-a]pyridine in rigid matrices by substitution effect." The Journal of organic chemistry vol. 78,6 (2013): 2482-9. doi: https://doi.org/10.1021/jo302711t
Mutai T, Sawatani H, Shida T, Shono H, Araki K. Tuning of excited-state intramolecular proton transfer (ESIPT) fluorescence of imidazo[1,2-a]pyridine in rigid matrices by substitution effect. J Org Chem. 2013 Mar 15;78(6):2482-9. doi: 10.1021/jo302711t. Epub 2013 Feb 13. PMID: 23405828.
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In-silico docking based design and synthesis of [1H,3H] imidazo[4,5-b] pyridines as lumazine synthase inhibitors for their effective antimicrobial activity.

Journal of pharmacy & bioallied sciences

Harer SL, Bhatia MS.
PMID: 25400412
J Pharm Bioallied Sci. 2014 Oct;6(4):285-96. doi: 10.4103/0975-7406.142962.

PURPOSE: The imidazopyridine moiety is important pharmacophore that has proven to be useful for a number of biologically relevant targets, also reported to display antibacterial, antifungal, antiviral properties. Riboflavin biosynthesis involving catalytic step of Lumazine synthase is absent in...

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Harer SL, Bhatia MS. In-silico docking based design and synthesis of [1H,3H] imidazo[4,5-b] pyridines as lumazine synthase inhibitors for their effective antimicrobial activity. J Pharm Bioallied Sci. 2014;6(4):285-96doi: 10.4103/0975-7406.142962.
Harer, S. L., & Bhatia, M. S. (2014). In-silico docking based design and synthesis of [1H,3H] imidazo[4,5-b] pyridines as lumazine synthase inhibitors for their effective antimicrobial activity. Journal of pharmacy & bioallied sciences, 6(4), 285-96. https://doi.org/10.4103/0975-7406.142962
Harer, Sunil L, and Bhatia, Manish S. "In-silico docking based design and synthesis of [1H,3H] imidazo[4,5-b] pyridines as lumazine synthase inhibitors for their effective antimicrobial activity." Journal of pharmacy & bioallied sciences vol. 6,4 (2014): 285-96. doi: https://doi.org/10.4103/0975-7406.142962
Harer SL, Bhatia MS. In-silico docking based design and synthesis of [1H,3H] imidazo[4,5-b] pyridines as lumazine synthase inhibitors for their effective antimicrobial activity. J Pharm Bioallied Sci. 2014 Oct;6(4):285-96. doi: 10.4103/0975-7406.142962. PMID: 25400412; PMCID: PMC4231389.
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Pharmacophore modeling, atom based 3D-QSAR and Molecular docking approaches to screen C-X-C chemokine receptor type 4 antagonists as microbicides for human immunodeficiency virus-1.

Virusdisease

Ramachandran R, Piramanyagam S.
PMID: 29291213
Virusdisease. 2017 Sep;28(3):272-280. doi: 10.1007/s13337-017-0397-1. Epub 2017 Sep 26.

The C-X-C chemokine receptor type 4 receptor CXCR4 which acts as a co-receptor for human immunodeficiency virus-1, expressed in the later stages of infection is considered as an attractive and new target for drug design. Microbicides acting as co-receptor...

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Ramachandran R, Piramanyagam S. Pharmacophore modeling, atom based 3D-QSAR and Molecular docking approaches to screen C-X-C chemokine receptor type 4 antagonists as microbicides for human immunodeficiency virus-1. Virusdisease. 2017;28(3):272-280doi: 10.1007/s13337-017-0397-1.
Ramachandran, R., & Piramanyagam, S. (2017). Pharmacophore modeling, atom based 3D-QSAR and Molecular docking approaches to screen C-X-C chemokine receptor type 4 antagonists as microbicides for human immunodeficiency virus-1. Virusdisease, 28(3), 272-280. https://doi.org/10.1007/s13337-017-0397-1
Ramachandran, Radhika, and Piramanyagam, Shanmughavel. "Pharmacophore modeling, atom based 3D-QSAR and Molecular docking approaches to screen C-X-C chemokine receptor type 4 antagonists as microbicides for human immunodeficiency virus-1." Virusdisease vol. 28,3 (2017): 272-280. doi: https://doi.org/10.1007/s13337-017-0397-1
Ramachandran R, Piramanyagam S. Pharmacophore modeling, atom based 3D-QSAR and Molecular docking approaches to screen C-X-C chemokine receptor type 4 antagonists as microbicides for human immunodeficiency virus-1. Virusdisease. 2017 Sep;28(3):272-280. doi: 10.1007/s13337-017-0397-1. Epub 2017 Sep 26. PMID: 29291213; PMCID: PMC5684990.
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Synthesis of Imidazopyridines via Copper-Catalyzed, Formal Aza-[3 + 2] Cycloaddition Reaction of Pyridine Derivatives with α-Diazo Oxime Ethers.

The Journal of organic chemistry

Park S, Kim H, Son JY, Um K, Lee S, Baek Y, Seo B, Lee PH.
PMID: 28869378
J Org Chem. 2017 Oct 06;82(19):10209-10218. doi: 10.1021/acs.joc.7b01714. Epub 2017 Sep 19.

The Cu-catalyzed, formal aza-[3 + 2] cycloaddition reaction of pyridine derivatives with α-diazo oxime ethers in trifluoroethanol was used to synthesize imidazopyridines via the release of molecular nitrogen and elimination of alcohol. These methods enabled modular synthesis of a...

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Park S, Kim H, Son JY, et al. Synthesis of Imidazopyridines via Copper-Catalyzed, Formal Aza-[3 + 2] Cycloaddition Reaction of Pyridine Derivatives with α-Diazo Oxime Ethers. J Org Chem. 2017;82(19):10209-10218doi: 10.1021/acs.joc.7b01714.
Park, S., Kim, H., Son, J. Y., Um, K., Lee, S., Baek, Y., Seo, B., & Lee, P. H. (2017). Synthesis of Imidazopyridines via Copper-Catalyzed, Formal Aza-[3 + 2] Cycloaddition Reaction of Pyridine Derivatives with α-Diazo Oxime Ethers. The Journal of organic chemistry, 82(19), 10209-10218. https://doi.org/10.1021/acs.joc.7b01714
Park, Sangjune, et al. "Synthesis of Imidazopyridines via Copper-Catalyzed, Formal Aza-[3 + 2] Cycloaddition Reaction of Pyridine Derivatives with α-Diazo Oxime Ethers." The Journal of organic chemistry vol. 82,19 (2017): 10209-10218. doi: https://doi.org/10.1021/acs.joc.7b01714
Park S, Kim H, Son JY, Um K, Lee S, Baek Y, Seo B, Lee PH. Synthesis of Imidazopyridines via Copper-Catalyzed, Formal Aza-[3 + 2] Cycloaddition Reaction of Pyridine Derivatives with α-Diazo Oxime Ethers. J Org Chem. 2017 Oct 06;82(19):10209-10218. doi: 10.1021/acs.joc.7b01714. Epub 2017 Sep 19. PMID: 28869378.
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Iodine-promoted radical alkyl sulfuration of imidazopyridines with dialkyl azo compounds and elemental sulfur.

Organic & biomolecular chemistry

Gao YC, Huang ZB, Xu L, Li ZD, Lai ZS, Tang RY.
PMID: 30724304
Org Biomol Chem. 2019 Feb 20;17(8):2279-2286. doi: 10.1039/c8ob03191f.

Dialkyl azo compounds were found to be effective alkyl radical sources for direct alkyl sulfuration with imidazopyridines using elemental sulfur under metal-free conditions. Iodine, an inexpensive and mild reagent, could promote alkyl sulfuration. A variety of quaternary cyanoalkyl radicals...

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Gao YC, Huang ZB, Xu L, et al. Iodine-promoted radical alkyl sulfuration of imidazopyridines with dialkyl azo compounds and elemental sulfur. Org Biomol Chem. 2019;17(8):2279-2286doi: 10.1039/c8ob03191f.
Gao, Y. C., Huang, Z. B., Xu, L., Li, Z. D., Lai, Z. S., & Tang, R. Y. (2019). Iodine-promoted radical alkyl sulfuration of imidazopyridines with dialkyl azo compounds and elemental sulfur. Organic & biomolecular chemistry, 17(8), 2279-2286. https://doi.org/10.1039/c8ob03191f
Gao, Yong-Chao, et al. "Iodine-promoted radical alkyl sulfuration of imidazopyridines with dialkyl azo compounds and elemental sulfur." Organic & biomolecular chemistry vol. 17,8 (2019): 2279-2286. doi: https://doi.org/10.1039/c8ob03191f
Gao YC, Huang ZB, Xu L, Li ZD, Lai ZS, Tang RY. Iodine-promoted radical alkyl sulfuration of imidazopyridines with dialkyl azo compounds and elemental sulfur. Org Biomol Chem. 2019 Feb 20;17(8):2279-2286. doi: 10.1039/c8ob03191f. PMID: 30724304.
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3-Benzyl-6-bromo-2-(2-fur-yl)-3H-imidazo[4,5-b]pyridine.

Acta crystallographica. Section E, Structure reports online

Ouzidan Y, Rodi YK, Zouihri H, Essassi el M, Ng SW.
PMID: 21588069
Acta Crystallogr Sect E Struct Rep Online. 2010 Jun 30;66:o1874. doi: 10.1107/S160053681002475X.

In the title mol-ecule, C(17)H(12)BrN(3)O, the imidazopyridine ring system is almost coplanar with the furan ring [dihedral angle = 2.0 (3)°]. The benzyl phenyl ring is oriented at dihedral angles of 85.2 (2) and 85.5 (1)°, respectively, with respect...

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Ouzidan Y, Rodi YK, Zouihri H, et al. 3-Benzyl-6-bromo-2-(2-fur-yl)-3H-imidazo[4,5-b]pyridine. Acta Crystallogr Sect E Struct Rep Online. 2010;66:o1874doi: 10.1107/S160053681002475X.
Ouzidan, Y., Rodi, Y. K., Zouihri, H., Essassi, e. l. . M., & Ng, S. W. (2010). 3-Benzyl-6-bromo-2-(2-fur-yl)-3H-imidazo[4,5-b]pyridine. Acta crystallographica. Section E, Structure reports online, 66o1874. https://doi.org/10.1107/S160053681002475X
Ouzidan, Younès, et al. "3-Benzyl-6-bromo-2-(2-fur-yl)-3H-imidazo[4,5-b]pyridine." Acta crystallographica. Section E, Structure reports online vol. 66 (2010): o1874. doi: https://doi.org/10.1107/S160053681002475X
Ouzidan Y, Rodi YK, Zouihri H, Essassi el M, Ng SW. 3-Benzyl-6-bromo-2-(2-fur-yl)-3H-imidazo[4,5-b]pyridine. Acta Crystallogr Sect E Struct Rep Online. 2010 Jun 30;66:o1874. doi: 10.1107/S160053681002475X. PMID: 21588069; PMCID: PMC3006925.
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4-Allyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine monohydrate.

Acta crystallographica. Section E, Structure reports online

Ouzidan Y, Rodi YK, Zouihri H, Essassi el M, Ng SW.
PMID: 21588236
Acta Crystallogr Sect E Struct Rep Online. 2010 Jul 03;66:o1903. doi: 10.1107/S1600536810025122.

In the mol-ecule of the title compound, C(15)H(12)BrN(3)·H(2)O, the phenyl ring is coplanar with the imidazopyridine ring system [dihedral angle = 0.4 (1)°]. The water mol-ecule is disordered over two positions with occupancies of 0.58 (1) and 0.42 (1),...

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Ouzidan Y, Rodi YK, Zouihri H, et al. 4-Allyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine monohydrate. Acta Crystallogr Sect E Struct Rep Online. 2010;66:o1903doi: 10.1107/S1600536810025122.
Ouzidan, Y., Rodi, Y. K., Zouihri, H., Essassi, e. l. . M., & Ng, S. W. (2010). 4-Allyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine monohydrate. Acta crystallographica. Section E, Structure reports online, 66o1903. https://doi.org/10.1107/S1600536810025122
Ouzidan, Younès, et al. "4-Allyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine monohydrate." Acta crystallographica. Section E, Structure reports online vol. 66 (2010): o1903. doi: https://doi.org/10.1107/S1600536810025122
Ouzidan Y, Rodi YK, Zouihri H, Essassi el M, Ng SW. 4-Allyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine monohydrate. Acta Crystallogr Sect E Struct Rep Online. 2010 Jul 03;66:o1903. doi: 10.1107/S1600536810025122. PMID: 21588236; PMCID: PMC3007243.
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