Some Phenylthiourea Derivatives and their Antituberculous Activity

Doub, Leonard; Richardson, L. M.; Herbst, D. R.; Black, Martin L.; Stevenson, O. L.; Bambas, L. L.; Youmans, Guy P.; Youmans, Anne S.

doi:10.1021/ja01542a043

Cited by 45 publications

(14 citation statements)

References 3 publications

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“…On the other hand, functionalities bulkier than an allyl group at the R2 position also gave rise to almost complete loss of inhibition of mycobacterial growth. The fact that highest antituberculosis activity in phenylthioureas was observed for compounds with the terminal nitrogen substituted by a single short chain alkyl group, was also in agreement with previous reports [59,60].…”

Section: Triazole Compoundssupporting

confidence: 92%

“…Thiacetazone (A) with a thiosemicarbazone structure, has been reported as a tuberculostatic agent. In a previous work, Doub et al [59] revealed antituberculosis properties of a wide number of phenylthioureas (B). Glasser and Dougthy [60] also reported the same type of activity associated with a number of thiourea derivatives substituted with a heterocyclic ring at one nitrogen.…”

Section: Triazole Compoundsmentioning

confidence: 99%

“…with a substituted thiourea moiety In 2001, Kü çü kgü zel et al[61] reported the synthesis of a series of novel N-alkyl/aryltriazole-3-thione-5-yl)phenyl] thioureas(47)(48)(49)(50)(51)(52)(53)(54)(55)(56)(57)(58)(59)(60)(61)(62)(63)(64)(65) and three S-alkylated representatives of the former, N-alkyl/aryl-NO-…”

mentioning

confidence: 99%

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Thiourea, triazole and thiadiazine compounds and their metal complexes as antifungal agents

Rodríguez-Fernández

Manzano

Benito

et al. 2005

Journal of Inorganic Biochemistry

134

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Section: Triazole Compoundssupporting

confidence: 92%

Section: Triazole Compoundsmentioning

confidence: 99%

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Thiourea, triazole and thiadiazine compounds and their metal complexes as antifungal agents

Rodríguez-Fernández

Manzano

Benito

et al. 2005

Journal of Inorganic Biochemistry

134

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“…For instance, simpler substituted thioureas may be obtained, which bear resemblance to some of the phenylthiourea derivatives recently described by Doub et al (1958). These compounds have marked tuberculostatic activity , but this is of little import as antiviral and tuberculostatic activities rarely run parallel (Hurst and Hull, 1956); benzthiouracils could also be obtained, and substituted phenoxythiouracils have considerable antiviral activity (Bauer, 1955), but this route is rendered unlikely as the suggested mechanism for the formation of the benzthiouracil seems chemically improbable, although it might occur biologically.…”

Section: Discussionmentioning

confidence: 90%

The STRUCTURE‐ACTIVITY RELATIONSHIPS OF THE ANTIVIRAL CHEMOTHERAPEUTIC ACTIVITY OF ISATIN Β‐THIOSEMICARBAZONE

Bauer¹,

Sadler²

1960

British Journal of Pharmacology and Chemotherapy

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As part of an investigation devoted to the development of new antiviral agents a compound of established antiviral activity has been subjected to systematic structural modification. The structureactivity data so obtained have been used in the design of new compounds, some of which are described. The compound chosen was isatin f-thiosemicarbazone, which has high activity against neurovaccinia infection in mice, and a 4-point parallel-line assay of in vivo chemotherapeutic activity has been developed, which has enabled the activity of the derivatives to be determined against isatin f-thiosemicarbazone as a standard. The overall dimensions of the isatin /3-thiosemicarbazone molecule appear to be nearly maximal for the retention of high activity, as dll substituents in the aromatic ring decrease the activity irrespective of their nature or position. The projection of the -CS.NH2 group in relation to the ring nitrogen was found to be critical, as the a-thiosemicarbazone was inactive. A number of modifications of the side-chain were investigated: all led to reduction or loss of antiviral activity. The antiviral activity showed a positive correlation with chloroform solubility over a considerable range. The most active compound encountered was 1-ethylisatin f3-thiosemicarbazone, with an activity of 286 (isatin fl-thiosemicarbazone-100). Isatin g-thiosemicarbazone showed no activity against 15 other viruses, and 20 related compounds showed no activity against ectromelia.The antiviral effect of isatin /3-thiosemicarbazone (I) against vaccinia virus was first observed by Thompson, Minton, Officer, and Hitchings (1953), who found that mice receiving a diet containing 0.6% of the compound were protected against intracerebral infection with about 100 LD50 of the virus. Their experiments were not designed to demonstrate the maximum effect of the compound, and it was subsequently shown (Bauer, 1955)

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“…Heterocyclic thiourea compounds are known to exhibit antiviral [5], antituberculous [6], fungicidal [7], and herbicidal activities [8]. Some N-heterocyclic compounds (such as antipyrine) have been found to exhibit wide physiological activity [9].…”

Section: Introductionmentioning

confidence: 99%

A microwave-assisted solid-state synthesis and characterization of diheterocyclic thioureas

2006

Heteroatom Chem.

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Some Phenylthiourea Derivatives and their Antituberculous Activity

Cited by 45 publications

References 3 publications

Thiourea, triazole and thiadiazine compounds and their metal complexes as antifungal agents

Thiourea, triazole and thiadiazine compounds and their metal complexes as antifungal agents

The STRUCTURE‐ACTIVITY RELATIONSHIPS OF THE ANTIVIRAL CHEMOTHERAPEUTIC ACTIVITY OF ISATIN Β‐THIOSEMICARBAZONE

A microwave-assisted solid-state synthesis and characterization of diheterocyclic thioureas

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