Synthesis and acetylcholinesterase inhibitory activity of 2β,3α-disulfoxy-5α-cholestan-6-one
Disodium 2β,3α-dihydroxy-5α-cholestan-6-one disulfate (8) has been synthesized using cholesterol (1) as starting material. Sulfation was performed using trimethylamine-sulfur trioxide complex in dimethylformamide as the sulfating agent. The acetylcholinesterase inhibitory activity of compound 8 was...
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2011
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| LEADER | 10706caa a22010697a 4500 | ||
|---|---|---|---|
| 001 | PAPER-10330 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518204021.0 | ||
| 008 | 190411s2011 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-79960447804 | |
| 024 | 7 | |2 cas |a acetylcholinesterase, 9000-81-1; cholesterol, 57-88-5; n,n dimethylformamide, 68-12-2; oxide, 16833-27-5; sulfur trioxide, 7446-11-9; trimethylamine, 75-50-3; Acetylcholinesterase, 3.1.1.7; Steroids | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a STEDA | ||
| 100 | 1 | |a Richmond, V. | |
| 245 | 1 | 0 | |a Synthesis and acetylcholinesterase inhibitory activity of 2β,3α-disulfoxy-5α-cholestan-6-one |
| 260 | |c 2011 | ||
| 270 | 1 | 0 | |m Maier, M.S.; Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina; email: maier@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
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| 504 | |a Auto-Dock 4.0, The Scripps Research Institute, Department of Molecular Biology, MB-5, La Jolla, CA, 2007; Aburatani, M., Takeuchi, T., Mori, K., A simple synthesis of steroidal 3α,5-cyclo-6-ones and their efficient transformation to steroidal 2-en-6-ones (1987) Synthesis, 1987 (2), pp. 181-183 | ||
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| 504 | |a Khalid, A., Zaheer-ul-Haq, Anjum, S., Khan, M.R., Atta-ur-Rahman, Choudhary, M.I., Kinetics and structure-activity relationship studies on pregnane-type steroidal alkaloids that inhibit cholinesterases (2004) Bioorganic and Medicinal Chemistry, 12 (9), pp. 1995-2003. , DOI 10.1016/j.bmc.2004.03.002, PII S0968089604001622 | ||
| 504 | |a Zaheer-Ul-Haq, Wellenzohn, B., Liedl, K.R., Rode, B.M., Molecular Docking Studies of Natural Cholinesterase-Inhibiting Steroidal Alkaloids from Sarcococca saligna (2003) Journal of Medicinal Chemistry, 46 (23), pp. 5087-5090 | ||
| 520 | 3 | |a Disodium 2β,3α-dihydroxy-5α-cholestan-6-one disulfate (8) has been synthesized using cholesterol (1) as starting material. Sulfation was performed using trimethylamine-sulfur trioxide complex in dimethylformamide as the sulfating agent. The acetylcholinesterase inhibitory activity of compound 8 was evaluated and compared to that of disodium 2β,3α-dihydroxy- 5α-cholestane disulfate (10) and diols 7 and 9. Compounds 8 and 10 were active with IC50 values of 14.59 and 59.65 μM, respectively. Diols 7 and 9 showed no inhibitory activity (IC50 > 500 μM). © 2011 Elsevier Inc. All rights reserved. |l eng | |
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires, X124 | ||
| 536 | |a Detalles de la financiación: National Council for Scientific Research | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: We thank the University of Buenos Aires for financial support (Grant X124 ) of this work. V.R. thanks the National Research Council of Argentina (CONICET) for a Doctoral fellowship. A.P.M. and M.S.M. are Research Members of CONICET. | ||
| 593 | |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina | ||
| 593 | |a INQUISUR, Departamento de Química, Universidad Nacional Del sur, Avda. Alem 1253, 8000 Bahía Blanca, Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a ACETYLCHOLINESTERASE ACTIVITY |
| 690 | 1 | 0 | |a SULFATED STEROIDS |
| 690 | 1 | 0 | |a SYNTHESIS |
| 690 | 1 | 0 | |a 2 BETA,3 ALPHA DIHYDROXY 5 ALPHA CHOLESTANE DISULFATE |
| 690 | 1 | 0 | |a ACETYLCHOLINESTERASE |
| 690 | 1 | 0 | |a CHOLESTEROL |
| 690 | 1 | 0 | |a CHOLESTEROL MESYLATE |
| 690 | 1 | 0 | |a CHOLINESTERASE INHIBITOR |
| 690 | 1 | 0 | |a DISODIUM 2 BETA,3 ALPHA DIHYDROXY 5 ALPHA CHOLESTAN 6 ONE DISULFATE |
| 690 | 1 | 0 | |a N,N DIMETHYLFORMAMIDE |
| 690 | 1 | 0 | |a OXIDE |
| 690 | 1 | 0 | |a SULFUR TRIOXIDE |
| 690 | 1 | 0 | |a TRIMETHYLAMINE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a DRUG ACTIVITY |
| 690 | 1 | 0 | |a DRUG SULFATION |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a ENZYME ACTIVITY |
| 690 | 1 | 0 | |a ENZYME INHIBITION |
| 690 | 1 | 0 | |a IC 50 |
| 690 | 1 | 0 | |a IN VITRO STUDY |
| 690 | 1 | 0 | |a ACETYLCHOLINESTERASE |
| 690 | 1 | 0 | |a ENZYME ACTIVATION |
| 690 | 1 | 0 | |a KINETICS |
| 690 | 1 | 0 | |a MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a STEROIDS |
| 700 | 1 | |a Santos, G.A.G. | |
| 700 | 1 | |a Murray, A.P. | |
| 700 | 1 | |a Maier, M.S. | |
| 773 | 0 | |d 2011 |g v. 76 |h pp. 1160-1165 |k n. 10-11 |p Steroids |x 0039128X |w (AR-BaUEN)CENRE-577 |t Steroids | |
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