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14769-73-4

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14769-73-4 Usage

Pharmacology and mechanism of action

Levamisole is the L-isomer of tetramisole and is more active than the racemic mixture. It was introduced in 1966 as a veterinary drug and a little later as a human anthelminthic drug against ascariasis. The drug has also shown to be effective against hookworms (Ancylostoma duodenale and Necator americanus), but results of reported studies are inconsistent [1]. The mechanism of action of levamisole in helminthiasis is through its stimulation of autonomic ganglia (nicotinic receptors) of the worms. On exposure to the drug, immature and adult worms show spastic contraction followed by tonic paralysis. This mechanism seems to be common to other anthelminthics such as pyrantel and bephenium hydroxynaphthoate [2]. In higher doses, levamisole acts as an immunostimulant. It restores depressed cell-mediated immune mechanisms in peripheral T-lymphocytes, but may have marginal effects in immunologically competent individuals [3]. The clinical implication of this effect in the treatment of helminthiasis is unknown.

Indications

Different sources of media describe the Indications of 14769-73-4 differently. You can refer to the following data:
1. Monoinfections with Ascaris lumbricoides. In polyinfections, mebendazole is the drug of choice.
2. Levamisole (Ergamisol) is an antiparasitic drug that has been found to enhance T-cell function and cellular immunity. The drug improves survival of patients with resected colorectal cancers when combined with 5-fluorouracil; the mechanism of this interaction is not known. Levamisole does not have antitumor activity against established or metastatic cancer and has not been found useful in the adjuvant therapy of cancers other than colorectal cancer. The major adverse effects of levamisole are nausea and anorexia. Skin rashes, itching, flulike symptoms, and fevers also have been observed.
3. Levamisole (Ergamisol) was originally developed as an antihelminthic drug. It potentiates the stimulatory effects of antigens, mitogens, lymphokines, and chemotactic factors on lymphocytes, granulocytes, and macrophages. It has been shown to increase T cell–mediated immunity. Levamisole has been used successfully in treating chronic infections. It also has been approved for use in combination with fluorouracil in the treatment of colorectal cancer.

Side effects

Different sources of media describe the Side effects of 14769-73-4 differently. You can refer to the following data:
1. During the treatment of nematode infections the drug produces minor side effects including nausea, vomiting, abdominal pain and headache [4, 5]. During prolonged treatment as an immunomodulator in rheumatic arthritis and in cancer patients, serious side effects such as blood disorders (agranulocytosis, neutropenia and thrombocytopenia), kidney damage, influenza-like reactions, vasculitis, photosensitivity and allergy to the drug have been reported [6, 7].
2. Nausea, gastrointestinal upsets and very mild neurological problems have been reported.

Contraindications and precautions

The drug should be avoided in patients allergic to the drug. Administration of levamisole may provoke a reaction similar to that seen after intake of alcohol together with disulfiram. During long-term treatment, patients with kidney damage or with blood disorders may experience exacerbation of their diseases.

Interactions

Levamisole has been reported to displace the protein binding of rifampicin in vitro [8]. The clinical significance of this is as yet unknown.

Preparations

Available as levamisole hydrochloride: 118 mg is equivalent to 100 mg base. ? Ketrax? (Zeneca). Oral solution 40 mg base per 5 ml. Tablets 40 mg base. ? Solaskil? (Rh?ne-Poulenc Rorer). Tablets 30 mg base, 150 mg base. ? Ergamisol? (Lederle). Tablets 50 mg base. ? Levamisol? (Janssen). Tablets 50 mg base.

References

1. Miller MJ (1980). Use of levamisole in parasitic infections. Drugs, 19, 122–130. 2. van Wauwe J, Janssen PAJ (1991). On the biochemical mode of action of levamisole: an update. Int J Immunopharmacol, 13, 3–9. 3. Renoux G (1980). The general immunopharmacology of levamisole. Drugs, 19, 89–99. 4. Lionel ND, Mirando EH, Nanayakkara JC, Soysa PE (1969). Levamisole in the treatment of ascariasis in children. BMJ, 4, 340–341. 5. Farid Z, Bassily S, Miner WF, Hassan A, Laughli LW (1977). Comparative single-dose treatment of hookworm and roundworm infections with levamisole, pyrantel and bephenium. J Trop Med Hyg, 80, 107–108. 6. Chrisp P, McTavish D (1991). Levamisole/fluorouracil: A review of their pharmacology and adjuvant therapeutic use in colorectal cancer. Drugs & Aging, 14, 317–337. 7. Amery WK, Butterworth BS (1983) The dosage regimen of levamisole in cancer: is it related to efficacy and safety Int J Immunopharmacol, 5, 1–9. 8. Pérez-Gallardo L, Blanco ML, Soria H, Escanero JF (1992). Displacement of rifampicin bound to serum proteins by addition of levamisole. Biomed Pharmacother, 46, 173–174.

Originator

Solaskil,Specia,France,1971

Uses

Different sources of media describe the Uses of 14769-73-4 differently. You can refer to the following data:
1. Biological response modifier.
2. Levamisole is used for initial and secondary immunodeficient conditions, autoimmune diseases, chronic and reoccurring infections, large intestine adenocarcinoma, helmintosis, and rheumatoid arthritis. Synonyms of this drug are decaris, tetramizole, and others.Levimasole is also a drug of choice for ascardiasis. Numerous investigations show that a single dose of levamisole heals from 90 to 100% of patients with ascardiasis, in particular those infected with A. duodenale. It is less effective against ancylostomiasis and strongyloidiasis. However, it is not effective against N. americanus. It seems likely that it has a gangliostimulating effect on parasite tissues in both the parasympathetic and sympathetic regions. Moreover, it is presumed that this drug has an immunomodulatory effect on the host organism. Synonyms of this drug are decaris, solacil, ergamisol, tramisol, immunol, and others.

Definition

ChEBI: A 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole that has S configuration. It is used (generally as the monohydrochloride salt) to treat parasitic worm infections in pigs, sheep and cattle and was formerly used in huma s as an adjuvant to chemotherapy for the treatment of various cancers. It is also widely used as an adulterant to coccaine.

Manufacturing Process

To a stirred and refluxed suspension of 17 parts of 1,2-dibromoethane, 7.8 parts of sodium hydrogen carbonate and 50 parts of 2-propanol is added a mixture of 3.4 parts of dl-2-thio-1-phenyl-imidazolidine, 9 parts of a 20% potassium hydroxide solution in 40 parts of 2-propanol over a period of about 1 hour. After the addition is complete, the whole is stirred and refluxed for an additional 3 hours. The reaction mixture is evaporated. To the residue are added 18 parts of a 15% potassium hydroxide solution. The whole is extracted with toluene. The extract is dried and evaporated. The oily residue is dissolved in acetone and gaseous hydrogen chloride is introduced into the solution. The precipitated solid salt is filtered off and recrystallized from 2-propanol, yielding dl-2,3,5,6-tetrahydro-6-phenyl-imidazo[2,1-b]thiazole hydrochloride; melting point 264°C to 266°C.dl-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride, 188 g (0.785 mol), is suspended in a mixture of 500 ml of water and 500 ml of methylene chloride. The suspension is stirred mechanically while 20% sodium hydroxide solution is added until the solution is basic. Ice is added from time to time to keep the temperature below the boiling point of the methylene chloride. The methylene chloride layer is separated, washed with water, dried over potassium carbonate and evaporated. The oily residue crystallizes with the evolution of the heat when poured into a beaker containing 100 ml of ether. The free base is washed with ether. The yield of dl-6-phenyl-2,3,5,6- tetrahydroimidazo[2,-b]thiazole is 151.4 g (0.746 mol), 94%. The product has a melting point of 90°C.A solution of 204.3 g (1 mol) of dl-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1- b]thiazole and 232.3 g (1 mol) of d-10-camphorsulfonic acid in 1,750 ml of chloroform is allowed to crystallize overnight at -28°C. The solvate is recovered by filtration and washed with ice cold chloroform (400 ml). The solvate is dried (decomposed) under nitrogen 7 hours and then in air overnight. The yield of d(+)6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole d-10-camphorsulfonate is 202.5 g (0.464 mol) 92.8%, melting point 139°C to 140°C [α]D25+ 82.6 (C = 16, H2O).A solution of 150 g (0.344 mol) of d(+)6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole, d-10-camphorsulfonate in water is treated with 15.5 g (0.378 mol) of 98% sodium hydroxide and the liberated base extracted with chloroform. The chloroform solution is washed with water followed by sodium chloride solution and dried over magnesium sulfate. Evaporation of the solvent left 72.1 g of residue which crystallized shortly. The free base hereby obtained has a melting point of 60°C to 61.5°C and an optical rotation [α]D25+ 85.1 (C = 10, CHCl3).The free base d(+)6-phenyl-2,3,5.6-tetrahydroimidazo[2.1-b]thiazole is dissolved in 112 ml of acetone and 178 ml of isopropanolic hydrogen chloride is added all at once. The hydrochloride crystallizes at once. After cooling to below 0°C, the salt is recovered by filtration and washed with acetone. The product weighs 75.2 g (0.312 mol), 91%, from the camphorsulfonate, melting point 227°C to 227.5°C [α]D25+ 123.1 (C = 15, H2O).

Brand name

Ergamisol (Janssen).

Therapeutic Function

Antiinflammatory

Antimicrobial activity

Its principal activity is against Asc. lumbricoides and hookworms. Worms are paralyzed and passed out in the feces within a few hours.

Pharmaceutical Applications

The l-isomer of tetramisole, available as the monohydrochloride. The d-isomer has no anthelmintic activity. It is very soluble in water and is stable in the dry state.

Mechanism of action

Levamisole has immunomodulating activity. It is believed that it regulates cellular mechanisms of the immune system, and the mechanism of its action may be associated with activation and proliferative growth of T-lymphocytes, increased numbers of monocytes and activation of macrophages, and also with increased activity and hemotaxis of neutrophylic granulocytes. Levamisole also exhibits anthelmint action. It also increases the body’s overall resistivity and restores altered T-lymphocyte and phagocyte function. It can also fulfill an immunomodulatory function by strengthening the weak reaction of cellular immunity, weakening strong reaction, and having no effect on normal reaction.

Pharmacokinetics

Oral absorption: c. 90% Cmax 150 mg oral: 0.5 mg/L after c. 2 h Plasma half-life: c. 4 h Volume of distribution: 100–120 L Levamisole is rapidly absorbed from the gut and extensively metabolized in the liver. It is excreted chiefly in the urine.

Clinical Use

Ascariasis Hookworm infection Levamisole has been used in rheumatoid arthritis and some other conditions that are said to respond to its immunomodulatory activity.

Synthesis

Levamisole, 2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole (31.1.4), is synthesized in various ways. One of them begins with α-bromoacetophenone, the reaction of which with 2-imino-1,3-thiazolidine gives 3-phenacyl-2-imino-1,3-thiazolidine (31.1.1). Reacting this product with acetic anhydride gives 3-phenacyl-2-acetylimino-1,3- thiazolidine (31.1.2). The ketone group in the resulting compound is reduced to an alcohol using sodium borohydride, and the resulting hydroxyl group in (31.1.3) is replaced with chlorine using thionyl chloride. Heating the product in acetic anhydride, the imidazole cycle closes, forming the product (31.1.4). A somewhat different approach was realized when using styrene oxide as the initial starting material. Reacting it with 2-imino-1,3-thiazolidine gives 3-(2-phenyl-2-hydroxyethyl)- 2-imino-1,3-thiazolidine (31.1.5), which is subsequently treated with thionyl chloride and then acetic anhydride to give the desired levamisole (31.1.4). Finally, the following scheme of making the product has been proposed using the same styrene oxide. Styrene oxide is reacted with aziridine, forming 2-aziridion-1- phenylethanol-1 (31.1.6). Treating this with potassium isothiocyanate or thiourea gives 3- (2-phenyl-2-hydroxyethyl)-2-amino-1,3-thiazolidine (31.1.5), and subsequent treatment with thionyl chloride (such as described above) and then with acetic anhydride gives the desired levamisole (31.1.4).

Veterinary Drugs and Treatments

Depending on the product licensed, levamisole is indicated for the treatment of many nematodes in cattle, sheep and goats, swine, poultry. In sheep and cattle, levamisole has relatively good activity against abomasal nematodes, small intestinal nematodes (not particularly good against Strongyloides spp.), large intestinal nematodes (not Trichuris spp.), and lungworms. Adult forms of species that are usually covered by levamisole, include: Haemonchus spp., Trichostrongylus spp., Osteragia spp., Cooperia spp., Nematodirus spp., Bunostomum spp., Oesophagostomum spp., Chabertia spp., and Dictyocaulus vivapurus. Levamisole is less effective against the immature forms of these parasites, and is generally ineffective in cattle (but not sheep) against arrested larval forms. Resistance of parasites to levamisole is a growing concern. In swine, levamisole is indicated for the treatment of Ascaris suum, Oesophagostomum spp., Strongyloides, Stephanurus, and Metastrongylus. Levamisole has been used in dogs as a microfilaricide to treat Dirofilaria immitis infection in the past, but is rarely used today. It has also garnered some interest as an immunostimulant in the adjunctive therapy of various neoplasms. Because of its narrow margin for safety and limited efficacy against many equine parasites, levamisole is not generally used in horses as an antiparasitic agent. It has been tried as an immune stimulant, however.

Check Digit Verification of cas no

The CAS Registry Mumber 14769-73-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,7,6 and 9 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 14769-73:
(7*1)+(6*4)+(5*7)+(4*6)+(3*9)+(2*7)+(1*3)=134
134 % 10 = 4
So 14769-73-4 is a valid CAS Registry Number.
InChI:InChI=1/C11H12N2S.ClH/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10;/h1-5,10H,6-8H2;1H/t10-;/m1./s1

14769-73-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name levamisole

1.2 Other means of identification

Product number -
Other names l-tetramisole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Veterinary Drug: ANTHELMINTHIC_AGENT
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14769-73-4 SDS

14769-73-4Synthetic route

levamisole hydrochloride
16595-80-5

levamisole hydrochloride

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
With sodium hydroxide In diethyl ether; water Inert atmosphere;98%
With sodium hydroxide In water pH=12;98.32%
With sodium hydroxide In diethyl ether; water at 20℃; for 0.166667h;91%
carbon disulfide
75-15-0

carbon disulfide

(1S)-1-phenylethylene-1,2-diamine
62779-70-8

(1S)-1-phenylethylene-1,2-diamine

ethylene dibromide
106-93-4

ethylene dibromide

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
Stage #1: carbon disulfide; (1S)-1-phenylethylene-1,2-diamine In ethanol; water
Stage #2: ethylene dibromide With sodium carbonate In ethanol; water
65%
(S)-4-Phenyl-4,5-dihydro-1H-imidazole-2-thiol
16595-77-0

(S)-4-Phenyl-4,5-dihydro-1H-imidazole-2-thiol

ethylene dibromide
106-93-4

ethylene dibromide

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
With sodium carbonate In isopropyl alcohol60%
With sodium carbonate In isopropyl alcohol
(S)-3-(2'-hydroxy-2'-phenylethyl)-2-thiazolidinimine hydrochloride
112790-85-9

(S)-3-(2'-hydroxy-2'-phenylethyl)-2-thiazolidinimine hydrochloride

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
With thionyl chloride; potassium carbonate 1.)CH2Cl2, RT, 2 h, 2.) ethanol, reflux, 1 h; Yield given. Multistep reaction;
Tetramisole
5036-02-2

Tetramisole

Levamisole
14769-73-4

Levamisole

Tetramisole
5036-02-2

Tetramisole

A

Levamisole
14769-73-4

Levamisole

B

R-(+)-6-phenyl-2,3,5,6-tetrahydro-imidazo<2,1b>thiazole
14769-74-5

R-(+)-6-phenyl-2,3,5,6-tetrahydro-imidazo<2,1b>thiazole

Conditions
ConditionsYield
With pyrographite; O,O'-dibenzoyl-L-tartaric acid In carbon dioxide at 39℃; under 120010 Torr; Product distribution; Further Variations:; Reagents;
With O,O'-dibenzoyl-L-tartaric acid In dichloromethane; water at 40℃; Sonication; Irradiation; Overall yield = 84 %;A n/a
B n/a
(S)-3-(2'-hydroxy-2'-phenylethyl)-2-thiazolidinimine
112790-83-7

(S)-3-(2'-hydroxy-2'-phenylethyl)-2-thiazolidinimine

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
With thionyl chloride In dichloromethane
(S)-2-Amino-1-phenyl-1-ethanol
56613-81-1

(S)-2-Amino-1-phenyl-1-ethanol

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: imidazole
2: K2CO3; 18-crown-6 / Heating
3: TBAF / tetrahydrofuran
4: aq. ethanol / Heating
5: SOCl2 / CH2Cl2
View Scheme
N-(2-chloroethylamino)-1-phenyl-1-ethanol
121673-61-8

N-(2-chloroethylamino)-1-phenyl-1-ethanol

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. ethanol / Heating
2: SOCl2 / CH2Cl2
View Scheme
(S)-5-phenyl-1,3-oxazolidine-2-one
186343-35-1

(S)-5-phenyl-1,3-oxazolidine-2-one

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 79 percent / aq. NaOH / ethanol / Heating
2: imidazole
3: K2CO3; 18-crown-6 / Heating
4: TBAF / tetrahydrofuran
5: aq. ethanol / Heating
6: SOCl2 / CH2Cl2
View Scheme
(S)-2-((tert-butyldimethylsilyl)oxy)-2-phenylethanamine
848186-80-1

(S)-2-((tert-butyldimethylsilyl)oxy)-2-phenylethanamine

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: K2CO3; 18-crown-6 / Heating
2: TBAF / tetrahydrofuran
3: aq. ethanol / Heating
4: SOCl2 / CH2Cl2
View Scheme
N-(2-chloroethyl)-2-tert-butyldimethylsilyloxy-2-phenylethanamine
848186-81-2

N-(2-chloroethyl)-2-tert-butyldimethylsilyloxy-2-phenylethanamine

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: TBAF / tetrahydrofuran
2: aq. ethanol / Heating
3: SOCl2 / CH2Cl2
View Scheme
(1S)-1-phenylethylene-1,2-diamine
62779-70-8

(1S)-1-phenylethylene-1,2-diamine

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol; water
2: sodium carbonate / isopropyl alcohol
View Scheme
Multi-step reaction with 2 steps
1: water / ethanol
2: sodium carbonate / isopropyl alcohol
View Scheme
(S)-1-phenylethane-1,2-diamine dihydrochloride

(S)-1-phenylethane-1,2-diamine dihydrochloride

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide
2: ethanol; water
3: sodium carbonate / isopropyl alcohol
View Scheme
N-(benzylidene)-p-methylbenzenesulfonamide
51608-60-7

N-(benzylidene)-p-methylbenzenesulfonamide

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: C40H40N2O3; copper(II) acetate monohydrate / toluene / 36 h / 20 °C / Inert atmosphere; Molecular sieve
2: hydrogen; palladium on activated charcoal / methanol / 20 °C
3: magnesium / methanol / 0.83 h / Sonication
4: water; ethanol
View Scheme
(S)-4-methyl-N-(2-nitro-1-phenylethyl)benzenesulfonamide

(S)-4-methyl-N-(2-nitro-1-phenylethyl)benzenesulfonamide

Levamisole
14769-73-4

Levamisole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen; palladium on activated charcoal / methanol / 20 °C
2: magnesium / methanol / 0.83 h / Sonication
3: water; ethanol
View Scheme
Levamisole
14769-73-4

Levamisole

levamisole hydrochloride
16595-80-5

levamisole hydrochloride

Conditions
ConditionsYield
Stage #1: Levamisole With sodium metabisulfite; pyrographite In isopropyl alcohol for 0.5h;
Stage #2: With hydrogenchloride pH=4 - 5; Time;
92.1%
cisplatin
15663-27-1

cisplatin

Levamisole
14769-73-4

Levamisole

silver nitrate

silver nitrate

Pt(2+)*2NH3*C11H12N2S*Cl(1-)*NO3(1-)=[Pt(NH3)2(C11H12N2S)Cl](NO3)

Pt(2+)*2NH3*C11H12N2S*Cl(1-)*NO3(1-)=[Pt(NH3)2(C11H12N2S)Cl](NO3)

Conditions
ConditionsYield
In N,N-dimethyl-formamide stirring Pt-complex with 1 equiv. AgNO3 for 24 h in dark, filtration, addn. of 1 equiv. ligand, stirring for at least 3 h; solvent removal (reduced pressure), collection (filtration), washing (CH2Cl2), recrystn. (water); can be purified by reversed phase chromy. (C18stationary phase, water); elem. anal.; product is cis-isomer;79%
Levamisole
14769-73-4

Levamisole

silver nitrate

silver nitrate

Pt(2+)*2NH3*C11H12N2S*Cl(1-)*NO3(1-)=[Pt(NH3)2(C11H12N2S)Cl](NO3)

Pt(2+)*2NH3*C11H12N2S*Cl(1-)*NO3(1-)=[Pt(NH3)2(C11H12N2S)Cl](NO3)

Conditions
ConditionsYield
In N,N-dimethyl-formamide stirring Pt-complex with 1 equiv. AgNO3 for 24 h in dark, filtration, addn. of 1 equiv. ligand, stirring for at least 3 h; solvent removal (reduced pressure), collection (filtration), washing (CH2Cl2), recrystn. (water); can be purified by reversed phase chromy. (C18stationary phase, water); elem. anal.; product is trans-isomer;75%
cisplatin
15663-27-1

cisplatin

Levamisole
14769-73-4

Levamisole

Pt(2+)*NH2CH2CH2NH2*C11H12N2S*2Cl(1-)=[Pt(NH2CH2CH2NH2)(C11H12N2S)Cl]Cl

Pt(2+)*NH2CH2CH2NH2*C11H12N2S*2Cl(1-)=[Pt(NH2CH2CH2NH2)(C11H12N2S)Cl]Cl

Conditions
ConditionsYield
With AgNO3 In N,N-dimethyl-formamide stirring Pt-complex with 1 equiv. AgNO3 for 24 h in dark, filtration, addn. of 1 equiv. ligand, stirring for at least 3 h; solvent removal (reduced pressure), collection (filtration), washing (CH2Cl2), recrystn. (0.5 M HCl, then water); can be purified by reversed phase chromy. (C18 stationary phase, water); elem. anal.;75%
Levamisole
14769-73-4

Levamisole

1-Naphthyl isocyanate
86-84-0

1-Naphthyl isocyanate

(6S,11aΞ)-1,3-di-naphthalen-1-yl-6-phenyl-tetrahydro-thiazolo[2',3':2,3]imidazo[1,2-a][1,3,5]triazine-2,4-dione
65172-60-3

(6S,11aΞ)-1,3-di-naphthalen-1-yl-6-phenyl-tetrahydro-thiazolo[2',3':2,3]imidazo[1,2-a][1,3,5]triazine-2,4-dione

Conditions
ConditionsYield
In acetone
meso-tartaric acid
147-73-9

meso-tartaric acid

Levamisole
14769-73-4

Levamisole

levamisole D-tartrate

levamisole D-tartrate

Conditions
ConditionsYield
In ethanol
Levamisole
14769-73-4

Levamisole

citric acid
77-92-9

citric acid

levamisole citrate
32339-82-5

levamisole citrate

Conditions
ConditionsYield
In ethanol
Levamisole
14769-73-4

Levamisole

ascorbic acid
50-81-7

ascorbic acid

levamisole L-ascorbate
1400988-13-7

levamisole L-ascorbate

Conditions
ConditionsYield
In ethanol
3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

3-(4-hydroxy-3-methoxyphenyl)acrylic acid

Levamisole
14769-73-4

Levamisole

levamisole ferulate

levamisole ferulate

Conditions
ConditionsYield
In ethanol

14769-73-4Relevant articles and documents

Supercritical fluid extraction: A novel method for the resolution of tetramisole

Keszei, Sandor,Simandi, Bela,Szekely, Edit,Fogassy, Elemer,Sawinsky, Janos,Kemeny, Sandor

, p. 1275 - 1281 (1999)

A new resolution method, based on the selective distribution of enantiomers between a chiral solid and an achiral supercritical fluid phase, is reported. The chiral solid phase is formed from the optically active dicarboxylic acid derivative, (2R,3R)-O,O'-dibenzoyltartaric acid, and the racemic base (tetramisole). A new method is also described for the enrichment of enantiomeric mixtures which have an enantiomeric ratio other than 1:1. This is based on the partial salt formation of the enantiomeric mixture with an achiral substance, which is then followed by supercritical fluid extraction of the free enantiomer. The extract has an enantiomeric composition which is different from the starting mixture. The method is applied to an enantiomeric mixture of tetramisole with hydrochloric acid.

Effect of achiral support on the resolution of tetramisole by supercritical fluid extraction

Szekely, Edit,Simandi, Bela,Laszlo, Krisztina,Fogassy, Elemer,Pokol, Gyoergy,Kmecz, Ildiko

, p. 1429 - 1434 (2002)

The enantiomers of tetramisole were produced by partial diastereomeric salt formation with O,O′-dibenzoyl-(2R,3R)-tartaric acid monohydrate and subsequent supercritical fluid extraction (SFE) of the unreacted enantiomers in the presence of an achiral support. The effect of the activated carbon and Perfil 100 on the efficiency of chiral separation were studied. The kinetics of the process was found to be an important factor affecting enantioselectivity. When the parameters were properly set, much better resolution efficiency (F) and higher enantiomeric purity were achieved than in the equilibrium. The presence of Perfil 100 and activated carbon caused an increase as high as 53 and 84% in F, respectively, compared to that achieved without using any supporting material. Thus during the development of a resolution procedure, beside the proper resolution agent, optimised molar ratio and other parameters, the selection of achiral addict(s) may be also an important point.

Enantioselective aza-Henry reaction for the synthesis of (S)-levamisole using efficient recyclable chiral Cu(II)-amino alcohol derived complexes

Choudhary, Manoj K.,Tak, Rajkumar,Kureshy, Rukhsana I.,Ansari, Amamudin,Khan, Noor-Ul H.,Abdi, Sayed H.R.,Bajaj, Hari C.

, p. 85 - 93 (2015/09/07)

Chiral Cu(II) complexes were generated in situ by the interaction of aminoalcohol based ligands L1-L6 derived from (1R,2S)-(-)-2-aminodiphenylethanol, (1R,2S)-1-amino-2,3-dihydro-1H-inden-2-ol, (R or S)-valinol and (S)-2-amino-1,1-diphenylpropan-1-ol with 4-tert-butyl-2,6-diformylphenol and screened for aza-Henry reaction of a variety of aromatic, aliphatic N-tosylaldimine and aromatic N-benzenesulfonamide aldimine in toluene at RT. Excellent enantioselectivity, diastereoselectivity (99%) of β-nitro-N-tosylaldamine with good yield (80%) was achieved in case of complex L2-Cu(II) with low catalyst loading. The enantio-pure aza-Henry product obtained was straightforwardly transformed into the enantioenriched chiral vicinal diamine (ee; 96%) with good yield in successive two steps and was further used for the synthesis of (S)-levamisole (an anthelminthic agent). The catalytic system worked well up to five cycles with retention of enantioselectivity.

Oxazoline-based organocatalyst for enantioselective strecker reactions: A protocol for the synthesis of levamisole

Sadhukhan, Arghya,Sahu, Debashis,Ganguly, Bishwajit,Khan, Noor-Ul H.,Kureshy, Rukhsana I.,Abdi, Sayed H.R.,Suresh,Bajaj, Hari C.

supporting information, p. 14224 - 14232 (2013/11/06)

A chiral oxazoline-based or-ganocatalyst has been found to efficiently catalyze asymmetric Strecker reactions of various aromatic and aliphatic N-benzhydrylimines with trime-thylsilyl cyanide (TMSCN) as a cyanide source at -20°C to give α-aminoni-triles in high yield (96%) with excellent chiral induction (up to 98% ee). DFT calculations have been performed to rationalize the enantioselective formation of the product with the organo-catalyst in these reactions. The organo-catalyst has been characterized by single-crystal X-ray diffraction analysis, as well as by other analytical methods. This protocol has been extended to the synthesis of the pharmaceutically important drug molecule levamisole in high yield and with high enantioselectivity.

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