DE19607253A1 - New (E)-2-(4-di:methylamino)vinyl-benzoic acid derivatives - Google Patents

New (E)-2-(4-di:methylamino)vinyl-benzoic acid derivatives

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Publication number
DE19607253A1
DE19607253A1 DE1996107253 DE19607253A DE19607253A1 DE 19607253 A1 DE19607253 A1 DE 19607253A1 DE 1996107253 DE1996107253 DE 1996107253 DE 19607253 A DE19607253 A DE 19607253A DE 19607253 A1 DE19607253 A1 DE 19607253A1
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vinyl
benzoic acid
acid derivatives
new
methylamino
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Bernd Prof Dr Clement
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton

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  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

(E)-2-(4-dimethylamino)vinylbenzoic acid derivatives of formula (I) and their salts are new. R = 2-, 3- or 4-carboxylic acid group.

Description

(E)-2-(4-Dimethylamino)vinylbenzoesäurederivate der Formel I(E) -2- (4-Dimethylamino) vinylbenzoic acid derivatives of the formula I.

worin R eine Carbonsäurefunktion darstellt, die sich in Position 2, 3 oder 4 befindet und deren zugehörige Salze sind bisher noch nicht beschrieben worden, obwohl die analogen (E)-2-(4- Dimethylamino)vinylbenzoesäurenitrilderivate (M. Syz und Hch. Zollinger, 1965; K. Takaha­ schi et al., 1977) als mögliche Vorstufen und die unterschiedlichsten Methoden zur Darstellung von unsymmetrisch substituierten Stilbenderivaten (K. B. Becker, 1983) vielfach beschrieben wurden.wherein R represents a carboxylic acid function which is in position 2, 3 or 4 and their associated salts have not yet been described, although the analogous (E) -2- (4- Dimethylamino) vinylbenzoic acid nitrile derivatives (M. Syz and Hch. Zollinger, 1965; K. Takaha schi et al., 1977) as possible preliminary stages and the most varied methods of representation many times described by asymmetrically substituted stilbene derivatives (K. B. Becker, 1983) were.

Das Problem der Darstellung der (E)-4- und (E)-3-[2-(4-Dimethylamino)vinyl]benzoesäuren der Formel Ia, Ib wurde durch Verseifung der analogen Nitrilderivate im sauren Milieu gelöst. Die Reinigung der gewünschten Verbindungen erfolgte durch Sublimation im Vakuum (< 10-2 mbar).The problem of the preparation of the (E) -4- and (E) -3- [2- (4-dimethylamino) vinyl] benzoic acids of the formula Ia, Ib was solved by saponification of the analogous nitrile derivatives in an acidic medium. The desired compounds were cleaned by sublimation in vacuo (<10 -2 mbar).

(E)-2-[2-(4-Dimethylamino)vinyl]benzoesäure Ic konnte auf diesem Wege nicht erhalten wer­ den. Diese Problem wurde durch Kondensation von 4-Dimethylaminobenzaldehyd und Ethyl- 2-methylbenzoat in Anlehnung an ein Verfahren von K. Takahaschi et al., 1977 gelöst.(E) -2- [2- (4-Dimethylamino) vinyl] benzoic acid Ic could not be obtained in this way the. This problem was addressed by the condensation of 4-dimethylaminobenzaldehyde and ethyl 2-methylbenzoate based on a method by K. Takahaschi et al., 1977, solved.

Die besondere Bedeutung der dargestellten Verbindungen der Formel I liegt in deren Verwen­ dung als mögliche Arzneistoffe. Anionische Stilbenderivate zeigen z. B. Wirkungen als Kali­ umkanalblocker (T. Furukawa et al., 1993), Chloridkanalblocker (Lu et al., 1991) sowie eine antivirale Wirkung (HIV) (J. M. Salhany und L. M. Schopfer, 1993).The particular meaning of the compounds of formula I shown lies in their use as a possible drug. Anionic stilbene derivatives show e.g. B. Potash effects umkanalblocker (T. Furukawa et al., 1993), chloride channel blocker (Lu et al., 1991) and a antiviral activity (HIV) (J.M. Salhany and L.M. Schopfer, 1993).

Die Erfindung wird nachfolgend anhand genauer Versuchsbedingungen näher erläutert.The invention is explained in more detail below on the basis of precise test conditions.

Herstellung der 2-(4-Dimethylamino)vinylbenzoesäurederivatenPreparation of the 2- (4-dimethylamino) vinylbenzoic acid derivatives

Die als Ausgangsstoffe verwendeten 2-(4-Dimethylaminophenyl)vinylbenzonitrile wurden in Anlehnung an eine Methode von Takahashi et al., 1977 gewonnen.The 2- (4-dimethylaminophenyl) vinylbenzonitriles used as starting materials were in Based on a method by Takahashi et al., 1977.

(E)-2-[2-(4-Dimethylaminophenyl)vinyl]benzoesäure Ic. Zu einer Lösung von 2.47 g (22 mmol) KOBut in 15 ml DMPU wurde eine Lösung von 1.49 g (10 mmol) p-Dimethylamino­ benzaldehyd und 1.64 g (10 mmol) Ethyl-2-methylbenzoat in 5 ml DMPU unter Rühren und Stickstoffbegasung bei 10°C langsam zugetropft. Nach 8 Stunden Rühren wurde der Ansatz auf eine Lösung von 1.08 g (20 mmol) Ammoniumchlorid in 100 ml Eiswasser gegossen und dreimal mit je 100 ml Diethylether ausgeschüttelt. Einstellen der wäßrigen Phase mit Eisessig auf pH 5-6 ergab einen gelben Niederschlag, der abgesaugt und mit Wasser/Eisessig pH 5-6 gewaschen wurde. Nach dem Trocknen wurde der Niederschlag in siedendem Aceton eben gelöst und bis zur beginnenden Trübung mit Wasser versetzt. Absaugen der Kristalle nach ca. 1.5 Stunden, Waschen mit kaltem Aceton/Wasser und Trocknen ergab gelbgrüne Nadeln, Ausb.: 0.961 g (36% d. Th.), Schmp. 136°C (Zers.). - IR(KBr): = 3426 cm-1, 2892, 2804, 1678, 1606, 1592, 1524, 968. - ¹H NMR (360 MHz, [D₆]DMSO): δ = 2.94 (s, 6H, -N(CH₃)₂), 7.06 (mc, AA′BB′, 4H, Ar-H), 7.38 (mc, AB, ³J = 16.3 Hz, 2H, olef. H), 7.3 (t, 1H, Ar-H), 7.51 (mc, 1H, Ar-H), 7.8 (mc, 2H, Ar-H), 12.96 (br, 1H, -COOH). - ¹³C NMR (100 MHz, [D₆]Aceton): δ = 39.86 (2C, -N(CH₃)₂), 112.61, 122.68, 126.36, 126.51, 128.17, 131.08, 131.75, 132.25 (10C, C-2, -3, -3′, -4′, -5, -5′, -6, -6′, -CH=CH-), 126.11, 128.77, 140.09, 150.89 (4C, C-1, -1′, -2′, -4), 168.51 (1C, -COOH).
C₁₇H₁₇NO₂ (267.33)
Ber.: C 76.38, H 6.41, N 5.24;
Gef.: C 76.32, H 6.36, N 5.20.(E) -2- [2- (4-Dimethylaminophenyl) vinyl] benzoic acid Ic. To a solution of 2.47g (22 mmol) of KOBu t in 15 ml of DMPU, a solution 1.49 g (10 mmol) of p-dimethylamino benzaldehyde and 1.64 g (10 mmol) was added ethyl 2-methylbenzoate in 5 ml of DMPU with stirring under nitrogen slowly added dropwise at 10 ° C. After stirring for 8 hours, the mixture was poured onto a solution of 1.08 g (20 mmol) of ammonium chloride in 100 ml of ice water and shaken out three times with 100 ml of diethyl ether each time. Adjusting the aqueous phase to pH 5-6 with glacial acetic acid gave a yellow precipitate, which was filtered off with suction and washed with water / glacial acetic acid pH 5-6. After drying, the precipitate was just dissolved in boiling acetone and water was added until turbidity began. Sucking off the crystals after about 1.5 hours, washing with cold acetone / water and drying gave yellow-green needles, Yield: 0.961 g (36% of theory), mp. 136 ° C (dec.). - IR (KBr): = 3426 cm -1 , 2892, 2804, 1678, 1606, 1592, 1524, 968. - 1 H NMR (360 MHz, [D₆] DMSO): δ = 2.94 (s, 6H, -N ( CH₃) ₂), 7.06 (mc, AA′BB ′, 4H, Ar-H), 7.38 (mc, AB, ³J = 16.3 Hz, 2H, olef. H), 7.3 (t, 1H, Ar-H), 7.51 (mc, 1H, Ar-H), 7.8 (mc, 2H, Ar-H), 12.96 (br, 1H, -COOH). - 13 C NMR (100 MHz, [D₆] acetone): δ = 39.86 (2C, -N (CH₃) ₂), 112.61, 122.68, 126.36, 126.51, 128.17, 131.08, 131.75, 132.25 (10C, C-2, - 3, -3 ′, -4 ′, -5, -5 ′, -6, -6 ′, -CH = CH-), 126.11, 128.77, 140.09, 150.89 (4C, C-1, -1 ′, - 2 ′, -4), 168.51 (1C, -COOH).
C₁₇H₁₇NO₂ (267.33)
Calculated: C 76.38, H 6.41, N 5.24;
Found: C 76.32, H 6.36, N 5.20.

(E)-3-[2-(4-Dimethylaminophenyl)vinyl]benzoesäure Ib. 0.248 g (1 mmol) (E)-3-[2-(4-Di­ methylaminophenyl)vinyl]benzonitril wurden mit 6 ml 50% Schwefelsäure 18 Stunden bei 100°C gerührt. Anschließend wurden 6 ml Wasser zugegeben und mit konzentriertem Ammoniak unter Eiskühlung der pH-Wert auf 3-4 eingestellt. Die ausgefallene Säure wurde abgesaugt und mit Wasser gewaschen. Ein Teil der ausgefallenen Säure wurde bei 180°C im Vakuum (< 10-2 mbar) sublimiert. Gelbes Pulver, Ausb.: 44% d. Th., Schmp. 220-222 °C (Zers.). - IR (KBr): = 3440 cm-1, 2850, 2590, 1682, 1630, 1606, 1578, 1522, 960. - ¹H NMR (400 MHz, [D₆]DMSO): δ = 2.95 (s, 6H, -N(CH₃)₂), 6.72 (d, 2H, Ar-H), 7.13 (mc, AB, ³J = 16.4 Hz, 2H, olef. H), 7.45 (mc, 3H, Ar-H), 7.77 (mc, 1H, Ar-H), 8.07 (s, 2H, Ar-H), 13 (br, 1H, -COOH). - ¹³C NMR (100 MHz, [D₆]Aceton): δ = 39.97 (2C, -N(CH₃)₂), 112.73, 128.22 (4C, C-2, -3, -5, -6), 123.16, 127.37, 127.97, 129.2, 130.45, 130.59 (6C, C-2′, -4′, -5′, -6′, -CH=CH-), 125.67, 131.42, 139.31, 151.06 (4C, C-1, -1′, -3′, -4), 167.21 (1C, -COOH).
C₁₇H₁₇NO₂ (267.33)
Ber.: C 76.38, H 6.41, N 5.24;
Gef.: C 76.37, H 6.33, N 5.22.(E) -3- [2- (4-Dimethylaminophenyl) vinyl] benzoic acid Ib. 0.248 g (1 mmol) of (E) -3- [2- (4-dimethylaminophenyl) vinyl] benzonitrile were stirred with 6 ml of 50% sulfuric acid at 100 ° C. for 18 hours. Then 6 ml of water were added and the pH was adjusted to 3-4 with concentrated ammonia while cooling with ice. The precipitated acid was filtered off and washed with water. Part of the precipitated acid was sublimed at 180 ° C in a vacuum (<10 -2 mbar). Yellow powder, yield: 44% of theory Th., Mp 220-222 ° C (dec.). - IR (KBr): = 3440 cm -1 , 2850, 2590, 1682, 1630, 1606, 1578, 1522, 960. - 1 H NMR (400 MHz, [D₆] DMSO): δ = 2.95 (s, 6H, - N (CH₃) ₂), 6.72 (d, 2H, Ar-H), 7.13 (mc, AB, ³J = 16.4 Hz, 2H, olef. H), 7.45 (mc, 3H, Ar-H), 7.77 (mc , 1H, Ar-H), 8.07 (s, 2H, Ar-H), 13 (br, 1H, -COOH). - 13 C NMR (100 MHz, [D₆] acetone): δ = 39.97 (2C, -N (CH₃) ₂), 112.73, 128.22 (4C, C-2, -3, -5, -6), 123.16, 127.37 , 127.97, 129.2, 130.45, 130.59 (6C, C-2 ′, -4 ′, -5 ′, -6 ′, -CH = CH-), 125.67, 131.42, 139.31, 151.06 (4C, C-1, - 1 ′, -3 ′, -4), 167.21 (1C, -COOH).
C₁₇H₁₇NO₂ (267.33)
Calculated: C 76.38, H 6.41, N 5.24;
Found: C 76.37, H 6.33, N 5.22.

(E)-4-[2-(4-Dimethylaminophenyl)vinyl]benzoesäure Ia. 0.248 g (1 mmol) (E)-4-[2-(4-Di­ methylaminophenyl)vinyl]benzonitril wurden mit 6 ml 50% Schwefelsäure 27 Stunden bei 90°C gerührt. Anschließend wurden 6 ml Wasser zugegeben und mit konzentriertem Ammoniak unter Eiskühlung der pH-Wert auf 3-4 eingestellt. Die ausgefallene Säure wurde abgesaugt und mit Wasser gewaschen. Ein Teil der ausgefallenen Säure wurde bei 180°C im Vakuum (< 10-2 mbar) sublimiert. Gelbes Pulver, Ausb.: 56% d. Th., Schmp. 330°C (Zers.). - IR (KBr): = 3440 cm-1, 2856, 1678, 1592, 1522, 962. - ¹H NMR (360 MHz, [D₆]DMSO): δ = 2.95 (s, 6H, -N(CH₃)₂), 7.1 (mc, AA′BB′, 4H, Ar-H), 7.76 (mc, AA′BB′, 4H, Ar-H), 7.17 (mc, AB, ³J = 16.4 Hz, 2H, olef. H), 12.81 (br, 1H, -COOH). - ¹³C NMR (90 MHz, [D₆]DMSO): δ = 40.38 (2C, -N(CH₃)₂), 112.63, 126.18, 128.5, 130.24 (8C, C-2, -2′, -3, -3′, -5, -5′, -6, -6′), 122.81, 131.93 (2C, -CH=CH-), 124.87, 128.78, 142.92, 150.82 (4C, C-1, -1′, -4, -4′), 167.65 (1C, -COOH).
C₁₇H₁₇NO₂ (267.33)
Ber.: C 76.38, H 6.41, N 5.24;
Gef.: C 76.40, H 6.32, N 5.24. (E) -4- [2- (4-Dimethylaminophenyl) vinyl] benzoic acid Ia. 0.248 g (1 mmol) of (E) -4- [2- (4-dimethylaminophenyl) vinyl] benzonitrile was stirred with 6 ml of 50% sulfuric acid at 90 ° C. for 27 hours. Then 6 ml of water were added and the pH was adjusted to 3-4 with concentrated ammonia while cooling with ice. The precipitated acid was filtered off and washed with water. Part of the precipitated acid was sublimed at 180 ° C in a vacuum (<10 -2 mbar). Yellow powder, yield: 56% of theory Th., Mp. 330 ° C (dec.). - IR (KBr): = 3440 cm -1 , 2856, 1678, 1592, 1522, 962. - 1 H NMR (360 MHz, [D₆] DMSO): δ = 2.95 (s, 6H, -N (CH₃) ₂) , 7.1 (mc, AA′BB ′, 4H, Ar-H), 7.76 (mc, AA′BB ′, 4H, Ar-H), 7.17 (mc, AB, ³J = 16.4 Hz, 2H, olef. H) , 12.81 (br, 1H, -COOH). - 13 C NMR (90 MHz, [D₆] DMSO): δ = 40.38 (2C, -N (CH₃) ₂), 112.63, 126.18, 128.5, 130.24 (8C, C-2, -2 ′, -3, -3 ′, -5, -5 ′, -6, -6 ′), 122.81, 131.93 (2C, -CH = CH-), 124.87, 128.78, 142.92, 150.82 (4C, C-1, -1 ′, -4 , -4 ′), 167.65 (1C, -COOH).
C₁₇H₁₇NO₂ (267.33)
Calculated: C 76.38, H 6.41, N 5.24;
Found: C 76.40, H 6.32, N 5.24.

Literaturliterature

K. B. Becker: Synthesis of stilbenes. Synthesis 1983, 341-368.
M. Syz und Hch. Zollinger: Spektren und Basizität der reinen trans-Konfiguration von substitu­ ierten 4-Dimethylaminostilbenen. Helv. Chim. Acta 48, 517-523 (1965).
T. Furukawa, L. Virag, T. Sawanobori und M. Hiraoka: Stilbene disulfonates block ATP- sensitive K⁺ channels in guinea pig ventricular myocytes. J: Membr. Biol. 136, 289-302 (1993).
L. Lu, D. Markakis und W. Guggino: Blockade of calcium-dependent chloride current in Xe­ nopus oocytes by chloride channel blockers and antimalarial drugs. Cell. Physiol. Biochem. 1, 251-261 (1991).
J. M. Salhany und L. M. Schopfer: Pyridoxal 5′-phosphate binds specifically to soluble CD4 protem, HIV-1 receptor. Implications for AIDS therapy. J Biol. Chem. 268, 7643-7645 (1993).
K. Takahaschi, T. Okamoto, K. Yamada und H. Iida: A convenient synthesis of substituted stilbenes by condensation of o- or p-tolunitrile with p-substituted benzaldehydes. Synthesis 1977, 58-59.KB Becker: Synthesis of stilbenes. Synthesis 1983, 341-368.
M. Syz and Hch. Zollinger: Spectra and basicity of the pure trans configuration of substituted 4-dimethylaminostilbenes. Helv. Chim. Acta 48, 517-523 (1965).
T. Furukawa, L. Virag, T. Sawanobori and M. Hiraoka: Stilbene disulfonates block ATP-sensitive K⁺ channels in guinea pig ventricular myocytes. J: Membr. Biol. 136, 289-302 (1993).
L. Lu, D. Markakis and W. Guggino: Blockade of calcium-dependent chloride current in Xe nopus oocytes by chloride channel blockers and antimalarial drugs. Cell. Physiol. Biochem. 1, 251-261 (1991).
JM Salhany and LM Schopfer: Pyridoxal 5′-phosphate binds specifically to soluble CD4 protem, HIV-1 receptor. Implications for AIDS therapy. J Biol. Chem. 268, 7643-7645 (1993).
K. Takahaschi, T. Okamoto, K. Yamada and H. Iida: A convenient synthesis of substituted stilbenes by condensation of o- or p-tolunitrile with p-substituted benzaldehydes. Synthesis 1977, 58-59.

Claims (2)

1. (E)-2-(4-Dimethylamino)vinylbenzoesäuren der Formel I worin R eine Carbonsäurefunktion darstellt, die sich in Position 2, 3 oder 4 befindet und deren zugehörige Salze.1. (E) -2- (4-dimethylamino) vinylbenzoic acids of the formula I. wherein R represents a carboxylic acid function which is in position 2, 3 or 4 and their associated salts. 2. Verwendung der unter 1. beschriebenen 2-(4-Dimethylamino)vinylbenzoesäurederivate der Formel I und deren zugehörige Salze als Arzneistoffe.2. Use of the 2- (4-dimethylamino) vinylbenzoic acid derivatives described under 1 Formula I and their associated salts as drugs.
DE1996107253 1996-02-27 1996-02-27 New (E)-2-(4-di:methylamino)vinyl-benzoic acid derivatives Withdrawn DE19607253A1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108473862A (en) * 2015-11-16 2018-08-31 弗尔斯特博士研究院有限责任两合公司 For detecting in air, in solution and from wipe samples based on NOxExplosive fluorescent dye film

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108473862A (en) * 2015-11-16 2018-08-31 弗尔斯特博士研究院有限责任两合公司 For detecting in air, in solution and from wipe samples based on NOxExplosive fluorescent dye film
CN108473862B (en) * 2015-11-16 2021-03-12 弗尔斯特博士研究院有限责任两合公司 For detecting NO-based in air, in solution and from wiped samplesxFluorescent dye film of explosive
US11656213B2 (en) 2015-11-16 2023-05-23 Institut Dr. Foerster Gmbh & Co. Kg Fluorescent dye films for detecting NOx-based explosives in the air, in solutions, and from wipe samples

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