Skip to main content

Planarity of heteroaryldithiocarbazic acid derivatives showing tuberculostatic activity. IV. Diesters of benzoylcarbonohydrazonodithioic acid

Buy Article:

$51.00 plus tax (Refund Policy)

Dimethyl (3,4‐dichlorobenzoyl)carbonohydrazonodithioate, C10H10Cl2N2OS2, (D1), dibenzyl (3,4‐dichlorobenzoyl)carbonohydrazonodithioate, C22H18Cl2N2OS2, (D2), dimethyl (3,4‐dichlorobenzoyl)‐1‐methylcarbonohydrazonodithioate, C11H12Cl2N2OS2, (D3), 3,4‐dichloro‐N′‐(1,3‐dithiolan‐2‐ylidene)‐N‐methylbenzohydrazide, C11H10Cl2N2OS2, (D4), were synthesized as potential tuberculostatics. Compound (D1) (with two molecules in the asymmetric unit) was the only one showing tuberculostatic activity of the same range as the common drugs isoniazid and pyrazinamide. The molecular structures of the studied compounds depend on the substitution at the N atom adjacent to the carbonyl group. In the case of the unsubstituted derivatives (D1) and (D2), their central frames are generally planar with a twist of the 3,4‐dichlorophenyl ring by 30–40°. Until now, coplanarity of the aromatic ring with the (methylene)carbonohydrazone fragment has been considered a prerequisite for tuberculostatic activity. The N‐methylated derivatives (D3) and (D4) show an additional twist along the N—C(=O) bond by 20–30° due to the spatial repulsion introduced by the methyl substituent.
No References
No Citations
No Supplementary Data
No Data/Media
No Metrics

Document Type: Research Article

Publication date: 2012-03-15

  • Access Key
  • Free content
  • Partial Free content
  • New content
  • Open access content
  • Partial Open access content
  • Subscribed content
  • Partial Subscribed content
  • Free trial content
Cookie Policy
Cookie Policy
Ingenta Connect website makes use of cookies so as to keep track of data that you have filled in. I am Happy with this Find out more