635-41-6

Usage

Uses

Used in Pharmaceutical Industry:
Trimetozine is used as a sedative and tranquilizer for its mild tranquilizing effects in the treatment of anxiety.
Used in Urology:
Trimetozine is used as an antiurolithic agent to prevent the formation of kidney stones.
Used in Cosmetics Industry:
Trimetozine is used as a depigmentation agent to reduce skin pigmentation and even out skin tone.
Used in Radiation Protection:
Trimetozine is used as a radiation protectant to protect the skin and other tissues from the harmful effects of radiation exposure.

Originator

Opalene,Theraplix,France,1966

Manufacturing Process

46 g 3,4,5-trimethoxybenzoyl chloride are dissolved in 300 ml anhydrous benzene and 25 g triethylamine and thereafter 19 g anhydrous morpholine are added in small portions with ice-cooling. The solution is boiled for 2 hours under reflux. The precipitate is filtered off, and the solution is washed with dilute sulfuric acid, then with sodium hydrogen carbonate solution and finally with water, and then evaporated. The residual yellow oil soon crystallizes; the crystalline mass of the desired material is taken up with ether, filtered and then recrystallized from 90% ethanol, from which it separates in prisms. It is slightly soluble in water. Yield: 80%. melting point 120°C to 122°C.

Therapeutic Function

Sedative

InChI:InChI=1/C14H19NO5/c1-17-11-8-10(9-12(18-2)13(11)19-3)14(16)15-4-6-20-7-5-15/h8-9H,4-7H2,1-3H3

Upstream product

• 110-91-8 morpholine 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 35619-65-9 tritiozine 
• 118-41-2 Eudesmic acid 
• 25245-29-8 5-iodo-1,2,3-trimethoxybenzene 
• 201230-82-2 carbon monoxide 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 

Downstream Products

• 266329-23-1 (dimethylphenylsilyl)(3,4,5-trimethoxyphenyl)methanone 
• 889130-03-4 methyl (E)-3-(3,4,5-trimethoxyphenyl)-3-(dimethyl(phenyl)silyl)acrylate 
• 35619-65-9 tritiozine 

Relevant academic research and scientific papers

In situ protection and deprotection of amines for iron catalyzed oxidative amidation of aldehydes

An environmentally friendly synthetic route by the application of CO2 to synthesize amides via in situ protection and deprotection of amines for iron catalyzed oxidative amidation of aldehydes was developed. Various secondary and tertiary amides have been synthesized in moderate to good yields under mild and neutral reaction conditions. The use of amine hydrochloride salts and hence base for neutralization step is totally avoided in this protocol.

Double carbonylation of aryl iodides with amines under an atmospheric pressure of carbon monoxide using sulfur-modified Au-supported palladium

A double carbonylation of aryl iodides with amines proceeded smoothly under an atmospheric pressure of carbon monoxide by using palladium nanoparticles (Pd NPs) leached from a sulfur-modified Au-supported palladium material (SAPd), producing α-ketoamides in good to excellent yields. This journal is

Silica gel-mediated amide bond formation: An environmentally benign method for liquid-phase synthesis and cytotoxic activities of amides

An efficient, functional group tolerable, and environmentally benign process for the synthesis of amides was developed. No activation reagents or scavengers are required in this process. Purification of desired compounds is easy, rapid, and cost-effective. This protocol provides an alternative for the combinatorial liquid-phase synthesis of amide libraries for drug discovery. By this method, a number of amides were prepared and evaluated in vitro against a panel of human tumor cell lines. Cinnamic amide IV-4 was found to be the most potent compound synthesized against four human tumor cell lines.

Leishmanicidal potential of N-substituted morpholine derivatives: Synthesis and structure-activity relationships

A series of N-substituted morpholines 2-20 was synthesised by reacting various acid chlorides and alkyl halides with morpholine (1). All of the synthesised compounds 2-20 were screened for their leishmanicidal effects using amphotericin B (IC50 = 0.24 μg L-1) and pentamidine (IC50 = 2.56 μg mL-1) as standards and a structure-activity relationship (SAR) study was established. The compounds 2 (IC50 = 48 μg mL-1), 3 (IC50 = 30.0 μg mL-1), 10 (IC50 = 41.0 μg mL-1), 15 (IC50 = 33.0 μg mL-1), 16 (IC50 = 35.0 μg mL-1) and 20 (IC50 = 47.0 μg mL-1) showed weak leishmanicidal activities.

Chiral silanes via asymmetric hydrosilylation with catalytic CuH

CuH-catalyzed asymmetric conjugate reduction of β-silyl-α, β-unsaturated esters has been developed. Using PMHS as a stoichiometric source of hydride and in situ generated CuH ligated by Solvias' JOSIPHOS analogue PPF-P(t-Bu)2 leads to highly enantioselective 1,4-reductions.

Hydroxyphenstatin and the prodrugs thereof

The benzophenone derivative of combretastatin A-1, designated “hydroxyphenstatin”, was synthesized by compiling a protected bromobenzene and a benzaldehyde to form a benzhydrol which was subsequently oxidized to the ketone. Hydroxyphenstatin was converted

Antineoplastic agents. 443. Synthesis of the cancer cell growth inhibitor hydroxyphenstatin and its sodium diphosphate prodrug

A structure - activity relationship (SAR) study of the South African willow tree (Combretum caffrum) antineoplastic constituent combretastatin A-4 (3b) led to the discovery of a potent cancer cell growth inhibitor designated phenstatin (5a). This benzophenone derivative of combretastatin A-4 showed remarkable antineoplastic activity, and the benzophenone derivative of combretastatin A-1 was therefore synthesized. The benzophenone, designated hydroxyphenstatin (6a), was synthesized by coupling of a protected bromobenzene and a benzaldehyde to give the benzhydrol with subsequent oxidation to the ketone. Hydroxyphenstatin was converted to the sodium phosphate prodrug (6e) by a dibenzyl phosphite phosphorylation and subsequent benzyl cleavage (6a → 6d → 6e). While hydroxyphenstatin (6a) was a potent inhibitor of tubulin polymerization with activity comparable to that of combretastatin A-1 (3a), the phosphorylated derivative (6e) was inactive.

Synthesis and CNS-depressant profile of 3,4,5-trimethoxybenzoyl analogues

A series of 3,4,5-trimethoxybenzoyl analogues with varying electronic and stereochemical characteristics has been synthesized. Many of these compounds (4, 5, 9, 12, 15) showed appreciable potentiation of pentobarbitone-induced hypnosis. Several analogues (1, 5, 6, 11, 12, 15) exhibited marked reduction of spontaneous motor activity (SMA).