SU608802A1 - Bromine hydrates of substituted n-(benzimidazolyl-2-thioacetyl)-n-valerolactones showing analgetic activity, hypotensive and muscle relaxation effect and method of obtaining same - Google Patents

Description

In a dry three-necked flask equipped with a mechanical stirrer and reflux condenser, 3 g (0.02 mol) of pure 2-mercaptobenzimidazole, 30 ml of absolute ether are placed and 4.42 g (0.02 mol) of bromoacetyl valerolactone dissolved in 10 ml of absolute ether. The dissolution of 2-mercaptobenzimidazole crystals is immediately observed. Soon a product precipitates. Then stirred for 1 h at room temperature, the precipitate is filtered off, the filtrate is washed with dry acetone and dried in air. 6.40 g (86%) of the desired product are obtained, mp. 168-169 ° C.

Found,%: N 7.51; Br 21.37; S 8.50.

CuHisOsN SBr.

Calculated,%: N 7.55; Br 21.56; S 8.63.

Example 2. A-nzoamyl-y bromohydrate (benzimidazolyl-2-thioacetyl) -valerolactone is prepared analogously to example 1 from 1.5 g (0.01 mol) of 2-mercaptoisimidazole, 2.91 g (0.01 mol) a-isoamyl -U-bromoacetylvalerolactone and 20-30 ml of absolute ether. Yield 4.2 g (95.2%), t. Il. 150-151 ° C. White crystals, poorly soluble in water, soluble in acetone and alcohol.

Found,%: N 6.23; Br 18.00; S 7.13.

SShNgvOzKgZVg.

Calculated,%: N 6.35; Br 18.14; S 7.26.

Stroyiii proven spectral method.

In the IR spectra of both compounds, bands are absorbed, in the areas, vC O (ketone) 17CO; vC O (lactone) 1770; vC-O-C 1250. The benzimidazole ring is characterized by the following, their frequencies, vC C (arom.), 1620; vC C (skel.) 1520, 1540, 1560; vC-H (are.) 3040; vNH (bond) 3100-3400.

Example 3. A-isobutyl- (benzimidazolyl-2-thioacetyl) bromohydrate - ;; - valerolactone is prepared analogously to example 1 of 8.3 g (0.03 mol) of mercaptobenzimidazole, 40 ml of absolute ether or benzene. The yield of 9.7 g (82%), so pl. 157-158 ° C. White crystals, poorly soluble in water, dissolve in acetone, in alcohol.

Found,%: C 50.40; H 5.27; N 6.40; S 7.30; Вг 18.

CisHzsOsNaSBr.

Calculated,%: C 50.58; H 5.38; N 6.55; S 7.48; Br 18.03.

IR spectra are similar to Example 2. Example 4. A-butyl-7- (benz. Imidazolyl-2-thioacetyl) y-valerolactone bromohydrate is prepared in a manner similar to example 1 of 1.5 g (0.01 mol) of 2-mercaptobenzimidazole, 2.77 g (0.01 mol) of a-butyl-y-bromoacetyl-y-valerolactone and 20-30 ml of a mixture of absolute ether and acetone, stirring for 1 hour at room temperature, and the main product is precipitated, yield 3.4 g ( 80%), t. 147-148 ° C, in the form of white crystals, poorly soluble in water, soluble in acetone and alcohol.

Found,%: C 51.00; H 5.57; N 6.67; Br 17.90.

CjsHasBrOsNsS.

Calculated,%: C 50.59; H 5.40; N 6.56; Br 18.03.

IR spectra are similar to example 2.

Example 5. α-Butyl-β-carbethoxy-y- (benzimidazolyl-2-thioacetyl) -7-valerolactone bromohydrate is prepared as in Example 1 out of 10.47 g (0.03 mol) of was-butyl-y-carbethoxy-ubromoacetyl-y -valerolactoia, 4.5 g (0.03 mol) of 2-mercaptobenzimidazole in 40 ml of a mixture of absolute ether and acetone, stirring for 2 hours at room temperature. The yield of 12.85 g (83.3%), so pl. 154-155 ° C.

Found,%: C 50.18; H 5.60; N 5.76.

Calculated,%: C 50.50; H 5.41; N 5.61.

In the IR spectra, bands were absorbed; eni in the regions, vC O (el. Ether) 1735; vC O (ketone) 1705; v C O (lacto) 1770; vC-O-C 1250. The benzimidazole ring is characterized by the following, by their frequencies, CM-I: vC-C (arom.) 1620; (skele.) 1520, 1542, 1560; vC-H (are.) 3040; vNH (bond) 3100-3400.

Bromide hydrates mixed with - (benzimidazolyl-2-thioacetyl) -7-valerolactones, showing analgesic activity, hypotensive effect, muscular relaxation, its action is of interest as substances, expansion, and an arsenal of effects on a living organism.

Characteristics of the biological activity of the proposed compounds are presented in the table.

Hot technique

records, time

defensive

reflex (s) at the peak

drug action

18.1 ± 1.3

In example 1

20.1 ± 1.5 According to Example 2 Starch mucus (2%) 12.1 ± 0.8 50.4 ± 2.8 Amidopyrine

 The code of the drug 68-MOS, № 380775 dose of 100 mg / kg. The code of the drug 61-MOS, No. 380475, dose 10 mg / kg. 50 Known.

Studies show that the compounds described have analgesic activity comparable to the effects of medicinal substances used in practice.

Claims (2)

1. Bromide hydrates of mixed - (benzimidazolyl-2-thioacetyl) -u-valerolactones of the general formula NCS K c-s-CH.-oX) Nvgo rde, COOCaHs; , ISO-C4H9, uso-CsHii, exhibiting analgesic activity, hypothetical effect, muscle-relaxing effect.5 2. A method of producing compounds according to claim 1, characterized in that a-substituted β-bromoacetyl-y-valerolactones are reacted with 2-mercaptobenzimidazole in absolute ether medium or in a mixture with acetone, or benzene at room temperature for 0, 5-2 hours