With the aim to find new compounds with superior tranquilizer‐antidepressant activity theoretical studies, synthesis, X‐ray characterization and pharmacological test of the title compound were carried out. Theoretical studies suggested both tranquilizer and antidepressant activity and pharmacological tests proved it.

A study has been made of the fragmentation upon electron impact of 3,3‐dimethyl‐2,3,4,5,10,11‐hexahydro‐11‐phenyl‐1H‐dibenzo[b,e][1,4]diazepin‐1‐one and fifteen of its derivatives containing chloro, bromo, methyl, methoxy, hydroxy, nitro, amino, carboxyl and carboxymethyl substituents on ortho and para positions of the 11‐phenyl ring. All the spectra analyzed contain molecular ions and the principal fragmentation routes takes place either from the molecular or from (M+‐1) ion. There are, however, some deviations from the general fragmentation pattern in the case of 1,4‐dibenzodiazepin‐1‐ones with o‐nitro, o‐hydroxy and o‐carboxyl substituents caused by direct interactions of these groups with the benzodiazepine ring.

The pyrazole derivatives 3′-(2-R-phenyl)[3,2-c]pyrazole-16,24-epoxy-25-hydroxy-9,19-cyclostane Va -Vf have been prepared in a three step reaction from argentatin B. The structure of all the compounds synthesized was corroborated by 1 H and 13 C NMR, IR and mass spectroscopy.Argentatin B (I) is an abundant tetracyclic triterpene obtained 1 from the resin of the Mexican guayule (Parthenium argentatum A. GRAY). The skeleton of argentatin B has been found highly similar to steroidal ring and therefore a suitable target for the rational design of potentially useful steroidal-like active molecules. As an extension of our strategy for preparing other argentatin derivatives 2 , herein we report the synthesis of pyrazole derivatives of argentatin B as an attempt to pursue possible biologically active compounds. In this regard it has been reported the synthesis of some steroidallike molecules with pyrazole group fused to the ring A which are currently used as antiinflammatory drugs 3,4 . Our synthetic approach to prepare Va -Vf involves a Claisen-Schmidt condensation of argentatin B (I) with 2-substituted benzaldehydes IIa -IIf under basic medium to give intermediates IIIa -IIIf and subsequent condensation with hydrazine to furnish IVa -IVf. The final pyrazole derivatives Va -Vf were obtained upon treatment of IVa -IVf with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (Scheme 1).The IR data of IIIa -IIIf showed a characteristic band between 1 698 -1 675 cm −1 corresponding to α,β-unsaturated ketone in agreement with the expected ClaisenSchmidt condensation product (Table I). The 1 H NMR spectrum of IIIa -IIIf showed typical signals for the seven methyls 1,5 of argentatin B skeleton, one of them being secondary (δ 0.94 -0.95, J = 8 Hz, H-20) and six being tertiary (δ 0.95 -0.93, H-28;

Synthesis of Pyrazole Analogues from Argentatin B. -A facile three-step approach to prepare the pyrazole analogues of argentatin B (IV) (examples) is given. -(MARTINEZ, R.; LIMON, E.; DEL R. ARELLANO, M.; MARTINEZ, M.; BRITO, M.; Collect.

C21H21C1N20.½C2HsOH , M r = 375.9, monoclinic, C2/c, a=33.492(10), b=11.045(3), c= 28.902 (9) A, t= 130.68 (2) °, V= 8108 (1) ,/k 3, Z= 16, D x = 1.23 Mg m -a, ,~,(Cu Ka) = 1.54178/~,, /~ = 1.785 mm -l, F(000) = 3184, T= 300 K, R = 0.072 for 4100 observed reflections. Two independent molecules in the unit cell. The molecular structure is determined from the X-ray data and confirms the structure previously assigned on the basis of chemical and spectroscopic evidence. In both molecules the sevenmembered and cyclohexene rings adopt distorted boat and 1,2-diplanar conformations, respectively, and the benzodiazepine and cyclohexene ring junction is cis. The molecules in the crystal are held together by hydrogen bonds.