PL236000B1 - Chiral ebselen derivative of (1S, 3R, 4R)-2-[(S) -1-phenylethyl]-3-aminomethyl-2-azabicyclo[2.2.1]heptane and method of its preparation - Google Patents
Chiral ebselen derivative of (1S, 3R, 4R)-2-[(S) -1-phenylethyl]-3-aminomethyl-2-azabicyclo[2.2.1]heptane and method of its preparation Download PDFInfo
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- PL236000B1 PL236000B1 PL432309A PL43230918A PL236000B1 PL 236000 B1 PL236000 B1 PL 236000B1 PL 432309 A PL432309 A PL 432309A PL 43230918 A PL43230918 A PL 43230918A PL 236000 B1 PL236000 B1 PL 236000B1
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- azabicyclo
- phenylethyl
- heptane
- derivative
- chiral
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- DYEFUKCXAQOFHX-UHFFFAOYSA-N Ebselen Chemical class [se]1C2=CC=CC=C2C(=O)N1C1=CC=CC=C1 DYEFUKCXAQOFHX-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 title abstract description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims abstract description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 12
- -1 bicyclic amine Chemical class 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- VZUATBHEHMNOTC-ATGSNQNLSA-N [(1S,3R,4R)-2-[(1S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptan-3-yl]methanamine Chemical class C1(=CC=CC=C1)[C@H](C)N1[C@H]2CC[C@@H]([C@@H]1CN)C2 VZUATBHEHMNOTC-ATGSNQNLSA-N 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229950010033 ebselen Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GYLMCBOAXJVARF-UHFFFAOYSA-N 3-azabicyclo[2.2.1]heptane Chemical group C1C2CCC1NC2 GYLMCBOAXJVARF-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229960005475 antiinfective agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Abstract
Przedmiotem wynalazku jest chiralny ebselen pochodna (1S,3R,4R)-2-[(S)-1-fenyloetylo]-3-ammometylo-2-azabicyklo[2.2.1]heptanu, o wzorze 1. Wynalazek dotyczy również sposobu wytwarzania chiralnego ebselenu pochodnej (1S,3R,4R)-2-[(S)-1-fenyloetylo]-3-aminometylo-2-azabicyklo[2.2.1]heptanu, o wzorze 1, który polega na tym, że chlorek 2-(chloroseleno)benzoilu poddaje się reakcji z równomolową ilością bicyklicznej aminy w obecności trójetyloaminy oraz 4-dimetyloaminopirydyny (DMAP), w temperaturze 295 K, w środowisku rozpuszczalnika organicznego.The subject of the invention is a chiral ebselene derivative of (1S,3R,4R)-2-[(S)-1-phenylethyl]-3-ammomethyl-2-azabicyclo[2.2.1]heptane, formula 1. The invention also relates to a method for preparing chiral ebselen derivative of (1S,3R,4R)-2-[(S)-1-phenylethyl]-3-aminomethyl-2-azabicyclo[2.2.1]heptane, of formula 1, which consists in the fact that the chloride 2-( chloroselene)benzoyl is reacted with an equimolar amount of bicyclic amine in the presence of triethylamine and 4-dimethylaminopyridine (DMAP), at a temperature of 295 K, in an organic solvent.
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest chiralny ebselen pochodna (1S,3R,4R)-2-[(S)-1-fenyloetylo]-3-aminometylo-2-azabicyklo[2.2.1]heptanu, znajdujący zastosowanie w farmakologii oraz jako katalizator w syntezie organicznej.The subject of the invention is a chiral ebselene derivative of (1S, 3R, 4R) -2 - [(S) -1-phenylethyl] -3-aminomethyl-2-azabicyclo [2.2.1] heptane, used in pharmacology and as a catalyst in organic synthesis .
Przedmiotem wynalazku jest również sposób wytwarzania chiralnego ebselenu pochodnej (1S,3R,4R)-2-[(S)-1-fenyloetylo]-3-aminometylo-2-azabicyklo[2.2.1] heptanu.The invention also relates to a process for the preparation of the chiral ebselene of the derivative (1S, 3R, 4R) -2 - [(S) -1-phenylethyl] -3-aminomethyl-2-azabicyclo [2.2.1] heptane.
W literaturze przedmiotu, m.in. opisano, że ebselen (2-fenylo-1,2-benzizoselenazol-3(2H)-on) oraz jego pochodne mogą być stosowane w farmakologii jako antyutleniacze, środki przeciwzapalne, antynowotworowe, antyinfekcyjne, oraz inhibitory enzymów [Mugesh, G.: Chem. Rev. 2001, 101,In the literature on the subject, incl. describes that ebselen (2-phenyl-1,2-benzisoselenazol-3 (2H) -one) and its derivatives can be used in pharmacology as antioxidants, anti-inflammatory, anti-cancer, anti-infective agents, and enzyme inhibitors [Mugesh, G .: Chem . Rev. 2001, 101,
2125; Chem. Eur. J. 2008, 14, 10603; J. Am. Chem. Soc. 2010, 132, 5364; Nogueira, C.W. Chem. Rev. 2004, 104, 6255; Uchida, K. Chem. Res. Toxicol. 2006, 19, 1196]. Ze stanu techniki wiadomo, że ebselen oraz jego pochodne znalazły praktyczne zastosowanie w farmakologii, m.in. w kardiologii [Wang, X. CN 1572295 A], jako środki przeciwzapalne w ginekologii [Yang, X. CN 1709243 A], w leczeniu łuszczycy [Xiong, Z. CN 101019863 A] oraz infekcji bakteryjnych [Billack, B.C. US 20100227899 A1]. W literaturze przedmiotu opisano również zastosowanie ebselenu oraz jego pochodnych jako katalizatora transferu tlenu w wielu reakcjach chemicznych [Młochowski, J.: Molecules 2015, 20, 10205; Tetrahedron 2001,57, 9743; Kumar, S. J. Org. Chem. 2012, 77, 9541; Wirth, T. Heteroat. Chem. 2014, 25, 320].2125; Chem. Eur. J. 2008, 14, 10603; J. Am. Chem. Soc. 2010, 132, 5364; Nogueira, C.W. Chem. Rev. 2004, 104, 6255; Uchida, K. Chem. Res. Toxicol. 2006, 19, 1196]. It is known from the prior art that ebselen and its derivatives have found practical application in pharmacology, incl. in cardiology [Wang, X. CN 1572295 A], as anti-inflammatory agents in gynecology [Yang, X. CN 1709243 A], in the treatment of psoriasis [Xiong, Z. CN 101019863 A] and bacterial infections [Billack, B.C. US 20100227899 A1]. The literature on the subject also describes the use of ebselene and its derivatives as a catalyst for oxygen transfer in many chemical reactions [Młochowski, J .: Molecules 2015, 20, 10205; Tetrahedron 2001, 57,9743; Kumar, S. J. Org. Chem. 2012, 77, 9541; Wirth, T. Heteroat. Chem. 2014, 25, 320].
Syntezę i aktywność biologiczną wybranych chiralnych pochodnych zawierających szkielet 2-azanorbornylowy opisano w artykułach [Wojaczyńska, E. Org. Biomol. Chem. 2015, 13, 6116; Tetrahedron: Asymmetry 2016, 27, 753]. W literaturze przedmiotu opisano również zastosowanie pochodnych opisanych na w/w szkielecie w wielu syntezach stereoselektywnych [Andersson, P.G.: Synlett 2000, 1092; J. Org. Chem. 2002, 67, 1567; Tetrahedron: Asymmetry, 2002, 13, 447; Chem. Soc. Rev. 2002, 31, 223; J. Org. Chem. 2004, 69, 4885; Chem. Eur, J. 2006, 12, 2318; Loh, T.P. Tetrahedron Lett. 2008, 49, 6007].The synthesis and biological activity of selected chiral derivatives containing the 2-azanorbornyl skeleton are described in the articles [Wojaczyńska, E. Org. Biomol. Chem. 2015, 13, 6116; Tetrahedron: Asymmetry 2016, 27, 753]. The literature on the subject also describes the use of the derivatives described on the above-mentioned framework in many stereoselective syntheses [Andersson, P.G .: Synlett 2000, 1092; J. Org. Chem. 2002, 67, 1567; Tetrahedron: Asymmetry, 2002, 13, 447; Chem. Soc. Rev. 2002, 31, 223; J. Org. Chem. 2004, 69, 4885; Chem. Eur, J. 2006, 12, 2318; Loh, T.P. Tetrahedron Lett. 2008, 49, 6007].
Chiralny ebselen pochodna (1S,3R,4R)-2-[(S)-1-fenyloetylo]-3-aminometylo-2-azabicyklo[2.2.1]heptanu, będący przedmiotem wynalazku, nie został dotychczas opisany w literaturze naukowej i patentowej.The chiral ebselene derivative (1S, 3R, 4R) -2 - [(S) -1-phenylethyl] -3-aminomethyl-2-azabicyclo [2.2.1] heptane, which is the subject of the invention, has not yet been described in the scientific and patent literature .
Istotę wynalazku stanowi chiralny ebselen pochodna (1S,3R,4R)-2-[(S)-1-fenyloetylo]-3-aminometylo-2-azabicyklo[2.2.1]heptanu, o wzorze 1.The present invention is based on the chiral ebselene derivative (1S, 3R, 4R) -2 - [(S) -1-phenylethyl] -3-aminomethyl-2-azabicyclo [2.2.1] heptane, of formula 1.
Sposób wytwarzania chiralnego ebselenu pochodnej (1S,3R,4R)-2-[(S)-1-fenyloetylo]-3-aminometylo-2-azabicyklo[2.2.1]heptanu, o wzorze 1, według wynalazku polega na tym, że chlorek 2-(chloroseleno)benzoilu o wzorze 2 poddaje się reakcji z równomolową ilością bicyklicznej aminy przedstawionej wzorem 3 w obecności trójetyloaminy oraz 4-dimetyloaminopirydyny (DMAP), w temperaturze 295 K, w środowisku rozpuszczalnika organicznego.The method of producing chiral ebselene of the derivative (1S, 3R, 4R) -2 - [(S) -1-phenylethyl] -3-aminomethyl-2-azabicyclo [2.2.1] heptane, according to the invention, consists in the following: 2- (chloroselene) benzoyl chloride of formula II is reacted with an equimolar amount of the bicyclic amine represented by formula 3 in the presence of triethylamine and 4-dimethylaminopyridine (DMAP) at 295 K in an organic solvent.
Korzystnie jako rozpuszczalnik stosuje się bezwodny acetonitryl.Preferably, anhydrous acetonitrile is used as the solvent.
Zaletą tego sposobu jest możliwość otrzymania chiralnego ebselenu pochodnej (1S,3R,4R)-2-[(S)-1-fenyloetylo]-3-aminometylo-2-azabicyklo[2.2.1]heptanu, posiadającego sztywny układ bicykliczny, jakim jest szkielet 2-azabicyklo[2.2.1]heptanu charakteryzujący się stabilną konfiguracją oraz odpowiednio umieszczonymi centrami donorowymi.The advantage of this method is the possibility of obtaining chiral ebselene of the derivative (1S, 3R, 4R) -2 - [(S) -1-phenylethyl] -3-aminomethyl-2-azabicyclo [2.2.1] heptane having a rigid bicyclic system, which is 2-azabicyclo [2.2.1] heptane skeleton characterized by a stable configuration and appropriately placed donor centers.
Sposób według wynalazku umożliwia wytworzenie chiralnego ebselenu pochodnej (1S,3R,4R)-2-[(S)-1-fenyloetylo]-3-aminometylo-2-azabicyklo[2.2.1]heptanu o wzorze 1, z wysoką wydajnością i czystością.The process according to the invention makes it possible to prepare chiral ebselene of the derivative (1S, 3R, 4R) -2 - [(S) -1-phenylethyl] -3-aminomethyl-2-azabicyclo [2.2.1] heptane of formula 1 with high yield and purity .
P r z y k ł a d 1P r z k ł a d 1
W celu wytworzenia 2-[(1S,3R,4R)-2[(S)-1-fenyloetylo-2-azabicyklo[2.2.1]hept-3-ylo]metylo]-benzizoselenazol-3(2H)-onu, przedstawionego wzorem numer 1, do roztworu 1 mmola aminy 2aza-norbornylowej (0,230 g) o wzorze 3, otrzymanej metodą znaną z publikacji: Wojaczyńska, E.: Tetrahedron: Asymmetry 2016, 27, str. 753, w 3,0 mL suchego acetonitrylu wkrapla się roztwór chlorku 2-(chloroseleno)benzoilu (1 mmol, 0,267 g) w 3,0 mL suchego acetonitrylu. Następnie dodaje się trójetyloaminę (2,5 mmol, 3,5 mL) oraz szczyptę 4-dimetyloaminopirydyny (DMAP). Reakcję prowadzi się w temperaturze pokojowej (295 K) przez kilka dni. Rozpuszczalnik usuwa się na wyparce a surowy produkt oczyszcza chromatograficznie na silikażelu, stosując mieszaninę dichlorometanu i metanolu (10:1). Uzyskuje się 0,312 g (76%) 2-[(1S,3R,4R)-2[(S)-1-fenyloetylo-2-azabicyklo[2.2.1]hept-3-ylo]metylo]-benzizoselenazol-3(2H)-onu, w postaci jasno żółtego ciała stałego, którego tożsamość potwierdzają analizy spektroskopowe. 1H NMR (600 MHz, CDCh): δ = 1,16-1,21 (m, 1H), 1,25 (d, J = 9,8 Hz, 1H), 1,38 (d, J = 6,5 Hz, 4H), 1,50-1,63 (m, 1H), 1,83 (d, J = 10,1 Hz, 1H), 1,93-2,03To make 2 - [(1S, 3R, 4R) -2 [(S) -1-phenylethyl-2-azabicyclo [2.2.1] hept-3-yl] methyl] -benzisoselenazol-3 (2H) -one, 1, to a solution of 1 mmol of 2-a-norbornyl amine (0.230 g) of formula 3, obtained by the method known from Wojaczyńska, E .: Tetrahedron: Asymmetry 2016, 27, p. 753, in 3.0 mL of dry acetonitrile a solution of 2- (chloroselene) benzoyl chloride (1 mmol, 0.267 g) in 3.0 mL of dry acetonitrile is added dropwise. Then triethylamine (2.5 mmol, 3.5 mL) and a pinch of 4-dimethylaminopyridine (DMAP) are added. The reaction is carried out at room temperature (295 K) for several days. The solvent is removed in an evaporator and the crude product is purified by chromatography on silica gel using a mixture of dichloromethane and methanol (10: 1). 0.312 g (76%) of 2 - [(1S, 3R, 4R) -2 [(S) -1-phenylethyl-2-azabicyclo [2.2.1] hept-3-yl] methyl] -benzisoselenazol-3 ( 2H) -one, in the form of a light yellow solid, the identity of which is confirmed by spectroscopic analyzes. 1 H NMR (600 MHz, CDCl 3): δ = 1.16-1.21 (m, 1H), 1.25 (d, J = 9.8 Hz, 1H), 1.38 (d, J = 6, 5 Hz, 4H), 1.50-1.63 (m, 1H), 1.83 (d, J = 10.1 Hz, 1H), 1.93-2.03
PL 236 000 B1 (m, 1H), 2,22 (dd, J = 9,0, 2,5 Hz, 1H), 2,29 (d, J = 4,3 Hz, 1H), 2,45 (dd, J = 14,2, 2,5 Hz, 1H), 3,44 (dd, J = 14,3, 8,8 Hz, 1H), 3,51 (q, J = 6,5 Hz, 1H), 3,63 (s, 1H), 7,29-7,36 (m, 2H), 7,39 (t, J = 7,7 Hz, 2H), 7,45-7,56 (m, 4H), 7,93 (d, J = 7,8 Hz, 1H). 13C NMR (150 MHz, CDCb): 22,4, 22,5, 29,0, 35,5, 40,3, 48,3, 58,7, 61,2, 69,5, 123,8, 125,9, 127,3, 127,8, 128,7, 128,9, 131,7, 138,7, 145,9, 167,2. HRMS (ESI): wartości teoretyczne dla [C22H24N2OSe+H]+: 413,1127; wartości doświadczalne: 413,1115.PL 236,000 B1 (m, 1H), 2.22 (dd, J = 9.0, 2.5 Hz, 1H), 2.29 (d, J = 4.3 Hz, 1H), 2.45 ( dd, J = 14.2, 2.5 Hz, 1H), 3.44 (dd, J = 14.3, 8.8 Hz, 1H), 3.51 (q, J = 6.5 Hz, 1H ), 3.63 (s, 1H), 7.29-7.36 (m, 2H), 7.39 (t, J = 7.7Hz, 2H), 7.45-7.56 (m, 4H), 7.93 (d, J = 7.8 Hz, 1H). 13 C NMR (150 MHz, CDCb): 22.4, 22.5, 29.0, 35.5, 40.3, 48.3, 58.7, 61.2, 69.5, 123.8, 125.9, 127.3, 127.8, 128.7, 128.9, 131.7, 138.7, 145.9, 167.2. HRMS (ESI): theoretical values for [C22H24N2OSe + H] +: 413.1127; experimental values: 413.1115.
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