1-allylimidazole derivatives

FIELD: chemistry.

SUBSTANCE: invention relates to novel derivatives of 1-allylimidazole with metal salts , where R denotes allyl, E denotes a metal, e.g. Zn (II) or Co (II), An denotes chlorine or acetate, n equals 2.

EFFECT: novel 1-allylimidazole derivatives having antihypoxic activity are obtained.

1 cl, 7 tbl, 2 ex

 

The invention relates to new compounds of the number of metal complexes derived from 1-alkanolamide, in particular, 1-allylimidazole possessing biological activity, in particular, antihypoxic.

The search for new chemical compounds with pronounced antihypoxic activity in the different types of hypoxia, is an actual problem of modern pharmacology.

Known zinc complexes derived from bis 1-vinylimidazole and ethylvinylacetate having antihypoxic properties poisoning carbon monoxide (patents No. 2038079, No. 2115653) and cobalt as hemodilator (patent No. 2157813).

The purpose of the invention is a new metal complex compounds derived from 1-allylimidazole with valuable biological activity, in particular, antihypoxic properties for different types of hypoxia.

This goal is achieved by the synthesis of new complexes with derivatives of 1-allylimidazole and study of their biological activity in experimental pharmacological research.

Below are examples of the synthesis of new derivatives of 1-allylimidazole and the results of the study of their pharmacological activity.

Synthesis of complexes based on 1-allylimidazole

Example 1. Bis(1-allylimidazole) cobaltichloride (cipher CoAL)

Connect the s obtained at room temperature by adding a stoichiometric amount of cobalt chloride to the solution allylimidazole in ethanol. To a solution of 5,41 g (50.0 mmol) of 1-allylimidazole in 150 ml of absolute ethanol under stirring at room temperature for 30 min was added 5,94 g (25,0 mmol) CoCl2·H2O. Formed after 20 h stirring intense blue precipitate was filtered, washed with ether, dried in vacuum until constant weight was obtained 7,26 g (83,9%) bis(1-allylimidazole) cobalticyanide with TPL 122-123°C. the Product is soluble in water, acetone, chloroform, dimethylsulfoxide (DMSO), not soluble in ether, alcohol. The spectra of nuclear magnetic resonance (NMR) due to paramagnetism received complex to remove failed. IR spectrum, ν, cm-1: 554 CL, 591 CL, 627, 656, 750, 763, 778, 829, 857, 875 SL, 930, 952, 962 shoulder, 988, 995 shoulder, CL 1028, 1093 OS, 1108, 1116, 1220 SL, 1235, 1288, 1334 SL, SL 1343, 1397, 1419, 1443, 1452, 1509 shoulder, 1522, 1532, 1587 SL, 1612 SL, 1647 SL (C=CH2), 2940 SL, 2984 SL, 3017 SL, 3044 SL, 3112, 3131.

Found, %: C 41,94; N Br4.61; CL 20,34. C12H16N4Cl2Co. Calculated, %: 41,64; N. Of 4.66; N 16,19; Cl 20,49, With 17,02

The structural formula

Example 2. Bis(1-allylimidazole) cindicates (code ALL)

The compound obtained at room temperature by the addition of zinc acetate to a solution of allylimidazole [Zn(OAc)2:allylimidazole=1:2,0-2,2] in a mixture of acetone and ether (3:1).

To a solution 3,20 g (29.6 mmol) of 1-allylimidazole in 100 ml of a mixture of absolute ether: acetone (3:1) at first is mesheanii and room temperature was slowly added (within 0.5-1 h) of 2.54 g (to 13.8 mmol) of Zn(ASON 3)2. Formed after 48 h of stirring a white precipitate was filtered, washed with ether, dried in vacuum until constant weight was obtained of 5.24 g (94,9%) bis(1-allylimidazole)zincdiacetate with TPL 114-116°C. the Product is soluble in water, alcohol, acetone, chloroform, DMSO, insoluble in ether. An NMR spectrum1H, δ, ppm: 8.13 (1H, H2), 7.34 (1H, H5), 6.90 (1H, H4), 5.90 m (1H, CH=), 5.31 (1H, =CHCISI , JCIS=10.0 Hz), 5.23 (1H,=CHTRANSI , JTRANS=17.0 Hz), 4.56 (2H, NCH2, J=5.9 Hz), 2.06 (3H, Masao); NMR spectrum13S, δ, ppm: 179.02 (COO), 139.09 (2), 131.49 (CH=), 128.77 (4), 120.13 (5), 119.37 (=CH2), 50.32 (NCH2),23.12 (Masao). IR spectrum, ν, cm-1: 490 SL, 499 SL, SL 555, 586 SL, 621, 627 shoulder, 657, 663, 673 with, 750, 758, 776, 877, 890, 926, 936, 953 with, 991, 1010 SL, 1069 SL, 1094, 1108, 1240, 1284, 1293, 1333, 1388, 1440, 1515, 1535, 1585, 1619 s, 1646 (C=CH2), 2928 SL, 2991 CL, CL 3013, 3122.

Found, %: C 47,69; N 5,59; Zn 15,60. C16H22N4O4Zn. Calculated, %: 48,07; N. Of 5.55; N 14,02; Zn 16,36.

The structural formula is:

Study of the biological activity of derivatives of allylimidazole

The study was conducted in accordance with article 11 Declaration of Helsinki of the world medical Association (1964), International recommendations for conducting biomedical research with animals (1985) and laboratory Rules the practice in the Russian Federation (order of the Ministry of the Russian Federation No. 267 from 19.06.2003).

Research methodology

The experiments were conducted on 210 outbred mice-males weighing 20-23, Used adequate methods of experimental acute hypoxia [1]. In mice caused acute hypobaric hypoxia (AGBG) "recovery" with a speed of 50 m/s at a height of 10000 m above sea level in the chamber Vita, acute hypoxia with hypercapnia (Ohshc - placing each mouse in a transparent glass vessel with a capacity of 250 ml, acute gemicescuu hypoxia (Ageg) - introduction into the skin of the back of sodium nitrite (400 mg/kg), acute histotoxic hypoxia (AGTG) - introduction into the skin of the back of sodium nitroprusside (20 mg/kg). Experimental mice 1 hour prior to acute hypoxia was administered intraperitoneally in doses of 5-200 mg/kg of the compounds and the control animals in the same period and in the same way an equal volume of distilled water. Antihypoxic action of the substances evaluated by the lifespan of mice in minutes. The oxygen consumption of laboratory animals was determined using the apparatus of the closed type in the modification of Mitropolskogo (IV Sanotski, 1970) within 10 minutes after a 10-minute adaptation in the working chamber. The results of the measurements was calculated in ml per 1 minute per 100 g of body weight. Body temperature was measured electric thermometer in the rectum (O.N. Elizarova, 1974). Parameters of acute toxicity was determined by the method of Litchfield-Wilcox is on (M. Belenky, 1963). The digital data of the experiments were processed statistically using t-student criterion [2].

The results of the study

It is established that the magnitude and severity of antihypoxic effects depend on the compound, dose and models of hypoxia.

In terms of Ageg the lifespan of mice was increased among the studied derivatives allylimidazole (table 1) CoAL in four doses (10, 25, 50 and 100 mg/kg). While the lifespan of mice was increased by 46, 35, 55, and 77%, respectively. The drug under the code of ALL not have been effective.

Model Ohshc (table 2) increased the lifetime of the mice of both compounds. The severity of antihypoxic action and breadth of effective doses was more complex compounds ALL. So, ALL doses of 10, 25, 50 and 100 mg/kg increased the survival rate at 25, 29, 90 and 95%, a CoAL in these same doses of 17, 17, 42 and 38%, respectively. Drug comparison lipoxen had antihypoxic effect, increasing the life span of mice by 20, 33 and 27%.

High antihypoxic effect AGBG showed all connections, which in three doses increased the lifetime of mice 269, 197, 169, 255, 289 and 186% (table 3). Among the studied drugs comparison pronounced antihypoxic effect exerted lipoxen, increasing the life span of experimental mouse is in the doses of 50, 100 and 150 mg/kg 144, 151 and 166%.

In terms OGTG the lifespan of mice increased the connection under the code of CoAL in four doses (10, 25, 50 and 100 mg/kg) 17, 45, 67, and 83%, respectively (table 4). The connection under the code of ALL did not show antihypoxic effect. Among the drugs comparison pronounced antihypoxic effect exerted lipoxen, increasing the lifetime of animals at doses of 50 and 100 mg/kg, respectively, 40 and 94%.

All investigated compounds was significantly reduced oxygen consumption and body temperature (table 5, 6), which also indicates their antihypoxic activity.

Parameters of acute toxicity are shown in table 7.

Thus, the results of our experiments allow to conclude that the newly synthesized metal complexes derived allylimidazole are low-toxic and have a marked protective effects in models of acute hypoxia. Antihypoxic effect of these compounds on the latitude of the effective dose and the severity significantly exceeds that of the known antihypoxic drug lipoxen.

General formula 1 derived elimidate:

E - metal, such as Zn (II) or Co (II);

An anion CL-or CH3COOH-

Literature

1. Lukyanova L.D. Methodological guidelines for experimental study of p is aparatow, designed for the clinical study as antihypoxic funds. - M., 1990. - 18 S.

2. Samoilov NN. Table of values for the mean error and credible interval arithmetic average value of the variation range. - Tomsk, 1970. - 63 S.

Table 1
Comparative impact of new metal-complex compounds derived allylimidazole and lipoxen on the lifespan of mice in acute himicheskoi hypoxia compared with control taken as 100% (n=10)
№ p/pCipher chemical compoundDose, mg/kg
0,515102550100150200
1ALL---100±491±8108±3100±3- -
2CoALL--108±3146±8*135±7*155±4*177±4*--
3Lipoxen------111±2*119±2*110±6
Note.
1. The asterisk (*) denotes significant differences (P<0.05) as compared to control.
2. Sign (-) marked not used in the experiments dose.

Table 2
Comparative impact of new metal-complex compounds derived allylimidazole and lipoxen on the lifespan of mice under conditions of acute hypoxia with hypercapnia compared with control taken as 100% (n=10)
№ p/pCipher chemical compoundDose, mg/kg
15102550100150200
1ALL105±5115±3125±3*129±4*190±7*195±4*--
2CoALL--117±5*117±5*142±6*138±8*--
3Lipoxen----99±2120±7133±2*127±5*
Note.
1. The asterisk (*) denotes significant differences (P<0.05) as compared to control.
2. Sign (-) marked not used in the experiments dose.

Table 3
Comparative impact of new metal-complex compounds derived allylimidazole and lipoxen on the lifespan of mice in acute hypobaric hypoxia compared with control taken as 100% (n=10)
№ p/pCipher chemical compoundDose, mg/kg
0,515102550100150200
1ALL--130±5*349±8*389±7*284±10*310±8*--
2CoALL--123±6*151±6*168±8*271±9*286±7*--
3Lipoxen----110±18244±9251±7*266±8*123±18
Note.
1. The asterisk (*) denotes significant differences (P<0.05) as compared to control.
2. Sign (-) marked not used in the experiments dose.

Table 4
Comparative impact of new metal-complex compounds derived allylimidazole and lipoxen on the lifespan of mice in acute gistologicheskoe hypoxia compared with control taken as 100% (n=10)
is the p/p Cipher chemical compoundDose, mg/kg
0,515102550100150200
1ALL---108±892±1087±580±4--
2CoALL--108±2117±2*146±6*160±4*183±7*--
3Lipoxen----101±5140±3*194±2*115±8Note.
1. The asterisk (*) denotes significant differences (P<0.05) as compared to control.
2. Sign (-) marked not used in the experiments dose.

Table 5
The oxygen consumption of the mice with intraperitoneal injection of new metal-complex compounds, derivatives of imidazole
№ p/pCipher chemical compoundDose, mg/kgOxygen consumption, %
SourceAfter 1 hourAfter 3 hoursAfter 6 hoursAfter 24 hours
1ALL5010062±3*60±3*79±4*96±3
2CoALL5010 63±4*60±3*79±4*95±3
Note.
The asterisk (*) denotes significant differences (P<0.05) as compared with the initial value.

Table 6
The rectal temperature of mice with intraperitoneal injection of new metal-complex compounds, derivatives of imidazole
№ p/pCipher chemical compoundDose, mg/kgRectal temperature, %
SourceAfter 1 hourAfter 3 hoursAfter 6 hoursAfter 24 hours
1ALL5010095±0,8*81±1*95±0,7*100±1
2CoALL50 10092±2*91±1*92±1*100±1
Note.
The asterisk (*) denotes significant differences (P<0.05) as compared with the initial value.

Table 7
Acute toxicity of new metal-complex compounds, derivatives of imidazole intraperitoneal injection to mice
№ p/pCipher chemical compoundToxicity, mg/kg
LD16LD50LD84
1ALL125160185
2CoALL135160187

Derivatives of 1-allylimidazole General formula 1, having antihypoxic action

E - metal, for example: Zn (II) or Co (II),
'an, chloride or acetate,
n - 2.



 

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