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6-Chloro-3-(chloromethyl)-2-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide
S. NO. | PHYSICAL AND CHEMICAL PROPERTIES | |
1 | Molecular weight | 360.2 g/mol |
2 | Physical appearance | White crystalline powder |
3 | Melting point | 225oC |
4 | Solubility | Slightly soluble in alcohol; freely soluble in acetone |
5 | Octanol/water partition coefficient | 1.42 |
5 | Presence of ring | Benzothiazine |
6 | Number of chiral centers | Not present |
General structure activity of thiazide diuretics can be summarized as:
i. Cyclization of 5-chloro-2,4-disulfamoylaniline by using urea to get 7-sulfamoyl-6-chloro-3-oxo-3,4-dihydro-2H-1,2,4-benzothiadiazine-1,1-dioxide.
ii. Above formed compound is reacted with methyliodide in presence of sodiumhydride, taking DMF as solvent to get an intermediate compound (I).
(I) reacts with sodium hydroxide to give the compound (II).
(II) reacts with chloroacetaldehyde to get methyclothiazide.
Methyclothiazide is used for:
Side effects of methyclothiazide are:
Q.1 Mechanism of action of Methyclothiazide includes?
a) Prevention of active chloride reabsorption at the early distal tubule
b) Binding with thiazide sensitive Na-Cl transportor
c) None of these
d) Both a) and b)
Q.2 Therapeutic use of drug methyclothiazide is/are?
a) Management of diabetes
b) Treatment of Hypertension
c) Treatment of stable angina
d) All of the above
Q.3 Which of the following statement is correct related with the SAR of dihydropyridines calcium channel blockers?
a) Chlorothiazide is the simplest member of the series.
b) Hydrogen atom at the 2-N is most acidic due to presence of electron-withdrawing group.
c) Sulfonamide group at C-7 position provides additional acidity to the drug.
d) All of the above
Q.4 Number of chiral centers present in the structure of methyclothiazide?
a) 3
b) 2
c) 1
d) 0
Q.5 Correct sequence for the True/False for the physiochemical properties of the drug methyclothiazide can be?
I. Molecular weight = 246.3 gm/mol
II. Physical appearance = Colorless to yellowish liquid
III. Melting point = 173 oC
a) TFT
b) FFT
c) FFF
d) TTT
Q.6 Correct statements for the IUPAC nomenclatures of the drug are?
I. Methyclothiazide: 6-Chloro-3-(chloromethyl)-2-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide
II. Omeprazole: (RS)-6-(Difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1H-benzo[d]imidazole
III. Methysergide: (RS)-1-[(4-chlorophenyl)- phenyl-methyl]-4- [(4-tert-butylphenyl) methyl] piperazine
IV. 5-FU: 1-cyano-2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine
a) I, II, III, IV
b) III, IV
c) II, III, IV
d) I
Q.7 Match the following drugs with their correct classifications-
i. Methyclothiazide | A. Diuretics |
ii. Lansoprazole | B. Antimetabolite |
iii. Thioguanine | C. Antihyperlipidemic |
iv. Cholestipol | D. Proton pump inhibitor |
a) i-A, ii-C, iii-D, iv-B
b) i-A, ii-D, iii-B, iv-C
c) i-D, ii-B, iii-A, iv-C
d) i-D, ii-A, iii-C, iv-B
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ANSWERS
1-d
2-b
3-d
4-d
5-c
6-d
7-b
REFERENCES
[1] Lemke TL, Williams DA, editors. Foye’s principles of medicinal chemistry. Lippincott Williams & Wilkins; 2012 Jan 24.
2] Close, W.J. et al.: J. Am. Chem. Soc. (JACSAT) 82, 1132 (1960).
The post METHYCLOTHIAZIDE Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses appeared first on Gpatindia: Pharmacy Jobs, Admissions, Scholarships, Conference,Grants, Exam Alerts.
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