Methylisatin thiosemicarbazone

H4. Hansson, O., Johansson, S. G. 0., and Vahlquist, B., Vaccinia gangrenosa with normal humoral antibodies. A case possibly due to deficient cellular immunity treated with N-methylisatin-thiosemicarbazone (compound 33T57, Marboran). Acta Paediat. Scand. 66, 264-272 (1966). 

Bauer DJ, Stvincent L, Kempe CH, Downie AW (1963) Prophylactic treatment of small pox contacts with V-methylisatin beta-thiosemicarbazone (Compound 33t57, Marboran). Lancet 35 494 96... 

Methods for the analysis of the antiviral JV-methylisatin-3-thiosemi-carbazone have been reported.376 Metabolic removal of the sulfur from iV-methylisatin-3-thiosemicarbazone has been reported377 to give syn-and cmti-N-methylisatin-3-semicarbazone. 

An excess of isatin with thiocarbohydrazide gives 106.384 The syn isomer of isatin-3-thiosemicarbazone predominates while isatin-3-semicarbazone exists in the anti form.305 Treatment with acid or warming converts this anti form into the syn isomer, while base causes the reverse isomerization.344 4-Methylisatin-3-semicarbazone exists as the syn isomer.344... 

A-methylisatin-3-semicarbazone could be cyclized to the oxo analog of 108,399 but the cyclization of the thiosemicarbazone to 108 occurred much more easily.400 Similar treatment of isatin-3-semicarbazone led to 113 via ring opening of the isatin.400 In the A-acetyl series (98, R =... 

Among biologically active compounds - derivatives of isatin - there is methisazone (1-methylisatin 3-thiosemicarbazone), which has been used as a prophylactic agent against the smallpox virus [139-141], Methods for the synthesis of compounds with the general formula 146 have been developed in the search for new antiviral and antimicrobial agents [142] ... 

Synonyms. V-Methylisatin jS-Thiosemicarbazone Metisazone. Proprietary Name. Marboran 1 -Methylindoline-2,3-dione 3-thiosemicarbazone C,oH,oN40S = 234.3 CAS—1910-68-5... 

C10H9NO2 alpha-ethynyl benzene methanol carbamate 3567-38-2 25.00 1.2355 2 19077 C10H10N4OS N-methylisatin-3-(thiosemicarbazone) 1910-68-5 25.00 1.3493 2... 

Isatin-j8-thiosemicarbazone was originally found to be a potent antivaccinia viral agent in mice and the activity of this compound was attributed to complex formation [545]. Subsequently, a derivative, jV-methylisatin-3-thiosemicarbazone (M-IBT), proved to be a very effective antiviral agent in humans for the prevention of morbidity and mortality due to smallpox epide-... 

More recent work on metbisazone (Y-methylisatin-l -thiosemicarbazone) has extended its antiviral spectrum from purely DNA viruses to certain RNA viruses in tissue culture. These include foot-and-mouth disease, polio, certain rhinoviruses, some arboviruses and influenza A and B. The extent of inhibition is dose dependent and is said not to be due to any toxic effect on the cells in which the viruses are grown [165]. The possibility of using any of this class of compound for treatment of these diseases in man was thought improbable. 

Methisazone 6.19) (l-methylisatin-3-thiosemicarbazone, Marboran ) inhibits the multiplication of vaccinia virus in experimental animals. The antiviral action is extraordinarily high. Mice infected intracerebrally with 1000 mean lethal doses (LD50) of vaccinia (cowpox) virus required only 0.5 mg/kg for protection, and only 10 mg/kg was needed for protection against variola major... 

A series of N-acyl and N-acyloxymethyl isatin thiosemi-carbazones was synthesized in an attempt to expand the spectrum.These compounds were not inhibitors of influenza WSN or rhinovirus strains. N-methylisatin-P-4 4 -dibutyl-thiosemicarbazone was shown to be an inhibitor of poliovirus RNA synthesis.The compound directly inhibits cell-free polio RNA polymerase. 

Thiosemicarbazones - l-Methylisatin-3-thiosemicarbazone (methisazone "Marboran") prevented but did not cure smallpox in man and had a favorable effect on eczema vaccinatum and vaccinia gangrenosa A wider range of activity was seen in tissue culture with adeno, polio, varicella... 

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