The post TOLTERODINE Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses appeared first on Gpatindia: Pharmacy Jobs, Admissions, Scholarships, Conference,Grants, Exam Alerts.
]]>(S)-2-[3-(Diisopropylamino)-1-phenylpropyl]-4-methylphenol.
Tolterodine is an acetylcholine antagonist. It is a muscarinic antagonist.
S. NO. | PHYSICAL AND CHEMICAL PROPERTIES | |
1 | Molecular weight | 325.5 g/mol |
2 | Physical appearance | Solid |
3 | Melting point | 205°C. |
4 | Solubility | 12 mg/ml in water |
5 | Octanol/water partition coefficient | 5.6 |
6 | Presence of ring | Benzene |
7 | Number of chiral centers | 1 |
i. Condensation of p-cresol with cinnamic acid in tetralone media, in presence of sulfurinc acid at higher temperatures to produce 6-methyl-4-phenylchroman-2-one.
ii. Lactone ring opening with methanol and phenolic hydroxyl etherification to give 2-hydroxy-3-phenylpropanoate.
iii. The latter compound undergoes reduction to give 2-(3-hydroxy-1-phenylpropyl)-4-methylphenol.
iv. The last compound formed is tosylated with tosyl chloride in pyridine.
v. The product is reacted with diisopropylamine in acetonitrile to give an amine.
vi. Methyl fragment of amine is cleaved with phosphorous tribromide in dichloromethane to give a recemic mixture of tolterodine.
vii. Racemic tolterodine is resolved using tartaric L-(+)-tartaric acid to get the desired tolterodine. [2]
Tolterodine is used for:
Side effects of Tolterodine are:
Q.1 What can be the correct IUPAC nomenclature of Tolterodine?
a) (S)-2-[1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl] pyrrolidin-3-yl] -2,2-diphenyl-acetamide
b) (S)-2-[3-(Diisopropylamino)-1-phenylpropyl]-4-methylphenol.
c) 7-Chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylic acid
d) N,N-Dimethyl-2-[6-methyl-2-(4-methylphenyl)imidazo[1,2-a]pyridin-3-yl]acetamide hemitartrate
Q.2 Which amongst the following statements is/are incorrect related to the SAR of Tolterodine?
I. Either R1 or R2 must be heterocyclic or carbocyclic.
II. The R3 group can be hydrogen, hydroxyl, hydroxymethyl or amide.
III. Poorest derivatives has X as an ester.
IV. X can also be either oxygen or absent completely.
a) I, II
b) III
c) III, IV
d) II
Q.3 Corrects sequence of the steps involved in the synthesis of Tolterodine from p-cresol?
I. Condenstation with cinnamic acid
II. Tosylation
III. Reaction with diisoropylamine
IV. Lactone ring opening with methanol and esterification
V. Reduction
VI. Methyl fragmentation of amine using phosphorous tribromide
a) II – I – III – IV- VI – V
b)IV- II – I – III – VI – V
c) I- IV – V- II – III – VI
d) VI- I – II – IV- V – III
Q.4 Side effects of drug Tolterodine is/are?
a) Constipation
b) Headache
c) Dry mouth
d) All of the above
Q.5 Match the following drugs with their correct molecular weights-
i. Darifenacin | A.426.5 gm/mol |
ii. Tolterodine | B.307.4gm/mol |
iii. Chlorazepate | C. 325.5 gm/mol |
iv. Zolpidem | D. 314.72 gm/mol |
a) i-C, ii-B, iii-A, iv-D
b) i-C, ii-B, iii-D, iv-A
c) i-A, ii-C, iii-D, iv-B
d) i-B, ii-A, iii-D, iv-C
Q.6 An example of drug from class Acetylcholine antagonist?
a) Zolpidem
b) Chlorazepate
c) Amphetamine
d) Tolterodine
Q.7 The type of ring system found in the structure of Tolterodine?
a) Dihydrobenzofurane
b) Pyrrolopyrimidine
c) Benzene
d) Pyrrolopyrrole ring
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1-b
2-b
3-c
4-d
5-c
6-d
7-c
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