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Discovery of Benzotriazolo[4,3-d][1,4]diazepines as Orally Active Inhibitors of BET Bromodomains.

ACS medicinal chemistry letters

Taylor AM, Vaswani RG, Gehling VS, Hewitt MC, Leblanc Y, Audia JE, Bellon S, Cummings RT, Côté A, Harmange JC, Jayaram H, Joshi S, Lora JM, Mertz JA, Neiss A, Pardo E, Nasveschuk CG, Poy F, Sandy P, Setser JW, Sims RJ, Tang Y, Albrecht BK.
PMID: 26985289
ACS Med Chem Lett. 2015 Mar 25;7(2):145-50. doi: 10.1021/ml500411h. eCollection 2016 Feb 11.

Inhibition of the bromodomains of the BET family, of which BRD4 is a member, has been shown to decrease myc and interleukin (IL) 6 in vivo, markers that are of therapeutic relevance to cancer and inflammatory disease, respectively. Herein...

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Taylor AM, Vaswani RG, Gehling VS, et al. Discovery of Benzotriazolo[4,3-d][1,4]diazepines as Orally Active Inhibitors of BET Bromodomains. ACS Med Chem Lett. 2015;7(2):145-50doi: 10.1021/ml500411h.
Taylor, A. M., Vaswani, R. G., Gehling, V. S., Hewitt, M. C., Leblanc, Y., Audia, J. E., Bellon, S., Cummings, R. T., Côté, A., Harmange, J. C., Jayaram, H., Joshi, S., Lora, J. M., Mertz, J. A., Neiss, A., Pardo, E., Nasveschuk, C. G., Poy, F., Sandy, P., Setser, J. W., Sims, R. J., Tang, Y., & Albrecht, B. K. (2016). Discovery of Benzotriazolo[4,3-d][1,4]diazepines as Orally Active Inhibitors of BET Bromodomains. ACS medicinal chemistry letters, 7(2), 145-50. https://doi.org/10.1021/ml500411h
Taylor, Alexander M, et al. "Discovery of Benzotriazolo[4,3-d][1,4]diazepines as Orally Active Inhibitors of BET Bromodomains." ACS medicinal chemistry letters vol. 7,2 (2016): 145-50. doi: https://doi.org/10.1021/ml500411h
Taylor AM, Vaswani RG, Gehling VS, Hewitt MC, Leblanc Y, Audia JE, Bellon S, Cummings RT, Côté A, Harmange JC, Jayaram H, Joshi S, Lora JM, Mertz JA, Neiss A, Pardo E, Nasveschuk CG, Poy F, Sandy P, Setser JW, Sims RJ, Tang Y, Albrecht BK. Discovery of Benzotriazolo[4,3-d][1,4]diazepines as Orally Active Inhibitors of BET Bromodomains. ACS Med Chem Lett. 2015 Mar 25;7(2):145-50. doi: 10.1021/ml500411h. eCollection 2016 Feb 11. PMID: 26985289; PMCID: PMC4753545.
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[5+2] Cycloaddition of 2-(2-Aminoethyl)oxiranes with Alkynes via Epoxide Ring-Opening: A Facile Access to Azepines.

Angewandte Chemie (International ed. in English)

Hu C, Song RJ, Hu M, Yang Y, Li JH, Luo S.
PMID: 27457771
Angew Chem Int Ed Engl. 2016 Aug 22;55(35):10423-6. doi: 10.1002/anie.201604679. Epub 2016 Jul 26.

A new FeCl3 and BF3 ⋅OEt2 co-catalyzed tandem hetero-[5+2] cycloaddition of 2-(2-aminoethyl)oxiranes with a wide range of alkynes, including terminal alkynes and alkyl-substituted internal alkynes is presented. This is the first example of rapid and facile production of diverse...

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Hu C, Song RJ, Hu M, et al. [5+2] Cycloaddition of 2-(2-Aminoethyl)oxiranes with Alkynes via Epoxide Ring-Opening: A Facile Access to Azepines. Angew Chem Int Ed Engl. 2016;55(35):10423-6doi: 10.1002/anie.201604679.
Hu, C., Song, R. J., Hu, M., Yang, Y., Li, J. H., & Luo, S. (2016). [5+2] Cycloaddition of 2-(2-Aminoethyl)oxiranes with Alkynes via Epoxide Ring-Opening: A Facile Access to Azepines. Angewandte Chemie (International ed. in English), 55(35), 10423-6. https://doi.org/10.1002/anie.201604679
Hu, Chao, et al. "[5+2] Cycloaddition of 2-(2-Aminoethyl)oxiranes with Alkynes via Epoxide Ring-Opening: A Facile Access to Azepines." Angewandte Chemie (International ed. in English) vol. 55,35 (2016): 10423-6. doi: https://doi.org/10.1002/anie.201604679
Hu C, Song RJ, Hu M, Yang Y, Li JH, Luo S. [5+2] Cycloaddition of 2-(2-Aminoethyl)oxiranes with Alkynes via Epoxide Ring-Opening: A Facile Access to Azepines. Angew Chem Int Ed Engl. 2016 Aug 22;55(35):10423-6. doi: 10.1002/anie.201604679. Epub 2016 Jul 26. PMID: 27457771.
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Hyperpolarized xenon nuclear spins detected by optical atomic magnetometry.

Physical review letters

Yashchuk VV, Granwehr J, Kimball DF, Rochester SM, Trabesinger AH, Urban JT, Budker D, Pines A.
PMID: 15524968
Phys Rev Lett. 2004 Oct 15;93(16):160801. doi: 10.1103/PhysRevLett.93.160801. Epub 2004 Oct 11.

We report the use of an atomic magnetometer based on nonlinear magneto-optical rotation with frequency-modulated light to detect nuclear magnetization of xenon gas. The magnetization of a spin-exchange-polarized xenon sample (1.7 c m(3) at a pressure of 5 bars,...

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Yashchuk VV, Granwehr J, Kimball DF, et al. Hyperpolarized xenon nuclear spins detected by optical atomic magnetometry. Phys Rev Lett. 2004;93(16):160801doi: 10.1103/PhysRevLett.93.160801.
Yashchuk, V. V., Granwehr, J., Kimball, D. F., Rochester, S. M., Trabesinger, A. H., Urban, J. T., Budker, D., & Pines, A. (2004). Hyperpolarized xenon nuclear spins detected by optical atomic magnetometry. Physical review letters, 93(16), 160801. https://doi.org/10.1103/PhysRevLett.93.160801
Yashchuk, V V, et al. "Hyperpolarized xenon nuclear spins detected by optical atomic magnetometry." Physical review letters vol. 93,16 (2004): 160801. doi: https://doi.org/10.1103/PhysRevLett.93.160801
Yashchuk VV, Granwehr J, Kimball DF, Rochester SM, Trabesinger AH, Urban JT, Budker D, Pines A. Hyperpolarized xenon nuclear spins detected by optical atomic magnetometry. Phys Rev Lett. 2004 Oct 15;93(16):160801. doi: 10.1103/PhysRevLett.93.160801. Epub 2004 Oct 11. PMID: 15524968.
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1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: Exploration of suitable chemistry for library development.

Tetrahedron

Woo GH, Beeler AB, Snyder JK.
PMID: 19112520
Tetrahedron. 2007 Jun 18;63(25):5649-5655. doi: 10.1016/j.tet.2007.04.003.

The chemistry of 1,2,3,4-tetrahydro-1,5-naphthyridines and 2,3,4,5-tetrahydro-1H-pyrido[3,2-b]azepines has been explored with the goal of discovering reactions at N1 suitable for library development. Epoxide openings, palladium-catalyzed N-arylations, DEPBT-promoted acylations, and urea formation through the reaction with isocyanates were all successful. The...

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Woo GH, Beeler AB, Snyder JK. 1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: Exploration of suitable chemistry for library development. Tetrahedron. 2007;63(25):5649-5655doi: 10.1016/j.tet.2007.04.003.
Woo, G. H., Beeler, A. B., & Snyder, J. K. (2007). 1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: Exploration of suitable chemistry for library development. Tetrahedron, 63(25), 5649-5655. https://doi.org/10.1016/j.tet.2007.04.003
Woo, Grace H C, et al. "1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: Exploration of suitable chemistry for library development." Tetrahedron vol. 63,25 (2007): 5649-5655. doi: https://doi.org/10.1016/j.tet.2007.04.003
Woo GH, Beeler AB, Snyder JK. 1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: Exploration of suitable chemistry for library development. Tetrahedron. 2007 Jun 18;63(25):5649-5655. doi: 10.1016/j.tet.2007.04.003. PMID: 19112520; PMCID: PMC2608727.
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Time-of-flight flow imaging using NMR remote detection.

Physical review letters

Granwehr J, Harel E, Han S, Garcia S, Pines A, Sen PN, Song YQ.
PMID: 16196792
Phys Rev Lett. 2005 Aug 12;95(7):075503. doi: 10.1103/PhysRevLett.95.075503. Epub 2005 Aug 10.

A time-of-flight imaging technique is introduced to visualize fluid flow and dispersion through porous media using NMR. As the fluid flows through a sample, the nuclear spin magnetization is modulated by rf pulses and magnetic field gradients to encode...

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Granwehr J, Harel E, Han S, et al. Time-of-flight flow imaging using NMR remote detection. Phys Rev Lett. 2005;95(7):075503doi: 10.1103/PhysRevLett.95.075503.
Granwehr, J., Harel, E., Han, S., Garcia, S., Pines, A., Sen, P. N., & Song, Y. Q. (2005). Time-of-flight flow imaging using NMR remote detection. Physical review letters, 95(7), 075503. https://doi.org/10.1103/PhysRevLett.95.075503
Granwehr, J, et al. "Time-of-flight flow imaging using NMR remote detection." Physical review letters vol. 95,7 (2005): 075503. doi: https://doi.org/10.1103/PhysRevLett.95.075503
Granwehr J, Harel E, Han S, Garcia S, Pines A, Sen PN, Song YQ. Time-of-flight flow imaging using NMR remote detection. Phys Rev Lett. 2005 Aug 12;95(7):075503. doi: 10.1103/PhysRevLett.95.075503. Epub 2005 Aug 10. PMID: 16196792.
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Near-zero-field nuclear magnetic resonance.

Physical review letters

Ledbetter MP, Theis T, Blanchard JW, Ring H, Ganssle P, Appelt S, Blümich B, Pines A, Budker D.
PMID: 21981529
Phys Rev Lett. 2011 Sep 02;107(10):107601. doi: 10.1103/PhysRevLett.107.107601. Epub 2011 Sep 01.

We investigate nuclear magnetic resonance (NMR) in near zero field, where the Zeeman interaction can be treated as a perturbation to the electron mediated scalar interaction (J coupling). This is in stark contrast to the high-field case, where heteronuclear...

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Ledbetter MP, Theis T, Blanchard JW, et al. Near-zero-field nuclear magnetic resonance. Phys Rev Lett. 2011;107(10):107601doi: 10.1103/PhysRevLett.107.107601.
Ledbetter, M. P., Theis, T., Blanchard, J. W., Ring, H., Ganssle, P., Appelt, S., Blümich, B., Pines, A., & Budker, D. (2011). Near-zero-field nuclear magnetic resonance. Physical review letters, 107(10), 107601. https://doi.org/10.1103/PhysRevLett.107.107601
Ledbetter, M P, et al. "Near-zero-field nuclear magnetic resonance." Physical review letters vol. 107,10 (2011): 107601. doi: https://doi.org/10.1103/PhysRevLett.107.107601
Ledbetter MP, Theis T, Blanchard JW, Ring H, Ganssle P, Appelt S, Blümich B, Pines A, Budker D. Near-zero-field nuclear magnetic resonance. Phys Rev Lett. 2011 Sep 02;107(10):107601. doi: 10.1103/PhysRevLett.107.107601. Epub 2011 Sep 01. PMID: 21981529.
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Atroposelective formation of dibenz[c,e]azepines via intramolecular direct arylation with centre-axis chirality transfer.

Organic & biomolecular chemistry

Cheetham CA, Massey RS, Pira SL, Pritchard RG, Wallace TW.
PMID: 21267501
Org Biomol Chem. 2011 Mar 21;9(6):1831-8. doi: 10.1039/c0ob00889c. Epub 2011 Jan 26.

5-Substituted 6,7-dihydrodibenz[c,e]azepines, a class of secondary amine incorporating a centre-axis chirality relay, are accessible from 1-substituted N-(2-bromobenzyl)-1-phenylmethanamines via N-acylation and ring-closing intramolecular direct arylation. The ring closure proceeds with high atropodiastereoselectivity due to strain effects that are induced by...

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Cheetham CA, Massey RS, Pira SL, et al. Atroposelective formation of dibenz[c,e]azepines via intramolecular direct arylation with centre-axis chirality transfer. Org Biomol Chem. 2011;9(6):1831-8doi: 10.1039/c0ob00889c.
Cheetham, C. A., Massey, R. S., Pira, S. L., Pritchard, R. G., & Wallace, T. W. (2011). Atroposelective formation of dibenz[c,e]azepines via intramolecular direct arylation with centre-axis chirality transfer. Organic & biomolecular chemistry, 9(6), 1831-8. https://doi.org/10.1039/c0ob00889c
Cheetham, Caroline A, et al. "Atroposelective formation of dibenz[c,e]azepines via intramolecular direct arylation with centre-axis chirality transfer." Organic & biomolecular chemistry vol. 9,6 (2011): 1831-8. doi: https://doi.org/10.1039/c0ob00889c
Cheetham CA, Massey RS, Pira SL, Pritchard RG, Wallace TW. Atroposelective formation of dibenz[c,e]azepines via intramolecular direct arylation with centre-axis chirality transfer. Org Biomol Chem. 2011 Mar 21;9(6):1831-8. doi: 10.1039/c0ob00889c. Epub 2011 Jan 26. PMID: 21267501.
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Liquid-state nuclear spin comagnetometers.

Physical review letters

Ledbetter MP, Pustelny S, Budker D, Romalis MV, Blanchard JW, Pines A.
PMID: 23004267
Phys Rev Lett. 2012 Jun 15;108(24):243001. doi: 10.1103/PhysRevLett.108.243001. Epub 2012 Jun 15.

We discuss nuclear spin comagnetometers based on ultralow-field nuclear magnetic resonance in mixtures of miscible solvents, each rich in a different nuclear spin. In one version thereof, Larmor precession of protons and 19F nuclei in a mixture of thermally...

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Ledbetter MP, Pustelny S, Budker D, et al. Liquid-state nuclear spin comagnetometers. Phys Rev Lett. 2012;108(24):243001doi: 10.1103/PhysRevLett.108.243001.
Ledbetter, M. P., Pustelny, S., Budker, D., Romalis, M. V., Blanchard, J. W., & Pines, A. (2012). Liquid-state nuclear spin comagnetometers. Physical review letters, 108(24), 243001. https://doi.org/10.1103/PhysRevLett.108.243001
Ledbetter, M P, et al. "Liquid-state nuclear spin comagnetometers." Physical review letters vol. 108,24 (2012): 243001. doi: https://doi.org/10.1103/PhysRevLett.108.243001
Ledbetter MP, Pustelny S, Budker D, Romalis MV, Blanchard JW, Pines A. Liquid-state nuclear spin comagnetometers. Phys Rev Lett. 2012 Jun 15;108(24):243001. doi: 10.1103/PhysRevLett.108.243001. Epub 2012 Jun 15. PMID: 23004267.
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External lumbar drain: A pragmatic test for prediction of shunt outcomes in idiopathic normal pressure hydrocephalus.

Surgical neurology international

Chotai S, Medel R, Herial NA, Medhkour A.
PMID: 24678428
Surg Neurol Int. 2014 Jan 27;5:12. doi: 10.4103/2152-7806.125860. eCollection 2014.

BACKGROUND: The consensus on most reliable supplemental test to predict the shunt responsiveness in patients with idiopathic normal pressure hydrocephalus (iNPH) is lacking. The aim of this study is to discuss the utility of external lumbar drain (ELD) in...

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Chotai S, Medel R, Herial NA, et al. External lumbar drain: A pragmatic test for prediction of shunt outcomes in idiopathic normal pressure hydrocephalus. Surg Neurol Int. 2014;5:12doi: 10.4103/2152-7806.125860.
Chotai, S., Medel, R., Herial, N. A., & Medhkour, A. (2014). External lumbar drain: A pragmatic test for prediction of shunt outcomes in idiopathic normal pressure hydrocephalus. Surgical neurology international, 512. https://doi.org/10.4103/2152-7806.125860
Chotai, Silky, et al. "External lumbar drain: A pragmatic test for prediction of shunt outcomes in idiopathic normal pressure hydrocephalus." Surgical neurology international vol. 5 (2014): 12. doi: https://doi.org/10.4103/2152-7806.125860
Chotai S, Medel R, Herial NA, Medhkour A. External lumbar drain: A pragmatic test for prediction of shunt outcomes in idiopathic normal pressure hydrocephalus. Surg Neurol Int. 2014 Jan 27;5:12. doi: 10.4103/2152-7806.125860. eCollection 2014. PMID: 24678428; PMCID: PMC3942611.
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Wide dynamic range magnetic field cycler: Harnessing quantum control at low and high fields.

The Review of scientific instruments

Ajoy A, Lv X, Druga E, Liu K, Safvati B, Morabe A, Fenton M, Nazaryan R, Patel S, Sjolander TF, Reimer JA, Sakellariou D, Meriles CA, Pines A.
PMID: 30709175
Rev Sci Instrum. 2019 Jan;90(1):013112. doi: 10.1063/1.5064685.

We describe the construction of a fast field cycling device capable of sweeping a 4-order-of-magnitude range of magnetic fields, from ∼1 mT to 7 T, in under 700 ms, and which is further extendable to a 1 nT-7 T...

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Ajoy A, Lv X, Druga E, et al. Wide dynamic range magnetic field cycler: Harnessing quantum control at low and high fields. Rev Sci Instrum. 2019;90(1):013112doi: 10.1063/1.5064685.
Ajoy, A., Lv, X., Druga, E., Liu, K., Safvati, B., Morabe, A., Fenton, M., Nazaryan, R., Patel, S., Sjolander, T. F., Reimer, J. A., Sakellariou, D., Meriles, C. A., & Pines, A. (2019). Wide dynamic range magnetic field cycler: Harnessing quantum control at low and high fields. The Review of scientific instruments, 90(1), 013112. https://doi.org/10.1063/1.5064685
Ajoy, A, et al. "Wide dynamic range magnetic field cycler: Harnessing quantum control at low and high fields." The Review of scientific instruments vol. 90,1 (2019): 013112. doi: https://doi.org/10.1063/1.5064685
Ajoy A, Lv X, Druga E, Liu K, Safvati B, Morabe A, Fenton M, Nazaryan R, Patel S, Sjolander TF, Reimer JA, Sakellariou D, Meriles CA, Pines A. Wide dynamic range magnetic field cycler: Harnessing quantum control at low and high fields. Rev Sci Instrum. 2019 Jan;90(1):013112. doi: 10.1063/1.5064685. PMID: 30709175.
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Computer-aided design of multi-target ligands at A.

Journal of cheminformatics

Kalash L, Val C, Azuaje J, Loza MI, Svensson F, Zoufir A, Mervin L, Ladds G, Brea J, Glen R, Sotelo E, Bender A.
PMID: 29290010
J Cheminform. 2017 Dec 30;9(1):67. doi: 10.1186/s13321-017-0249-4.

Compounds designed to display polypharmacology may have utility in treating complex diseases, where activity at multiple targets is required to produce a clinical effect. In particular, suitable compounds may be useful in treating neurodegenerative diseases by promoting neuronal survival...

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Kalash L, Val C, Azuaje J, et al. Computer-aided design of multi-target ligands at A. J Cheminform. 2017;9(1):67doi: 10.1186/s13321-017-0249-4.
Kalash, L., Val, C., Azuaje, J., Loza, M. I., Svensson, F., Zoufir, A., Mervin, L., Ladds, G., Brea, J., Glen, R., Sotelo, E., & Bender, A. (2017). Computer-aided design of multi-target ligands at A. Journal of cheminformatics, 9(1), 67. https://doi.org/10.1186/s13321-017-0249-4
Kalash, Leen, et al. "Computer-aided design of multi-target ligands at A." Journal of cheminformatics vol. 9,1 (2017): 67. doi: https://doi.org/10.1186/s13321-017-0249-4
Kalash L, Val C, Azuaje J, Loza MI, Svensson F, Zoufir A, Mervin L, Ladds G, Brea J, Glen R, Sotelo E, Bender A. Computer-aided design of multi-target ligands at A. J Cheminform. 2017 Dec 30;9(1):67. doi: 10.1186/s13321-017-0249-4. PMID: 29290010; PMCID: PMC5748027.
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Selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles via tandem reactions of alkynones with pyrrole derivatives.

Organic & biomolecular chemistry

Zhao Y, Yuan Y, Xu M, Zheng Z, Zhang R, Li Y.
PMID: 28731084
Org Biomol Chem. 2017 Aug 02;15(30):6328-6332. doi: 10.1039/c7ob01516j.

Novel methodologies for the selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles starting from pyrrole derivatives and alkynones are described. When reactions were carried out with 1,2,4-trisubstituted N-propargyl pyrroles using a ZnI

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Zhao Y, Yuan Y, Xu M, et al. Selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles via tandem reactions of alkynones with pyrrole derivatives. Org Biomol Chem. 2017;15(30):6328-6332doi: 10.1039/c7ob01516j.
Zhao, Y., Yuan, Y., Xu, M., Zheng, Z., Zhang, R., & Li, Y. (2017). Selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles via tandem reactions of alkynones with pyrrole derivatives. Organic & biomolecular chemistry, 15(30), 6328-6332. https://doi.org/10.1039/c7ob01516j
Zhao, Yulei, et al. "Selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles via tandem reactions of alkynones with pyrrole derivatives." Organic & biomolecular chemistry vol. 15,30 (2017): 6328-6332. doi: https://doi.org/10.1039/c7ob01516j
Zhao Y, Yuan Y, Xu M, Zheng Z, Zhang R, Li Y. Selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles via tandem reactions of alkynones with pyrrole derivatives. Org Biomol Chem. 2017 Aug 02;15(30):6328-6332. doi: 10.1039/c7ob01516j. PMID: 28731084.
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