An antibacterial and antifungal compound from .

p-Carboxyphenylazoxycyanide–dimethyl sulphoxide: an antibacterial and antifungal compound from Calvatia lilacina

“…The present analysis represents the first X-ray structure determination of an azoxycyano derivative and was undertaken in order to provide an unambiguous answer to these questions. The results are in agreement with the predictions of Gasco et al (1974) as far as the position of the oxygen atom in the azoxycyano group is concerned; 0(2) is actually bonded to the nitrogen atom adjacent to the benzene ring. The N(3)-O(2) distance is very short when compared with those found in azoxy compounds [1.279 A in p-azoxyanisole (Krigbaum, Chatani & Barber, 1970), 1.291 A in ethyl p-azoxybenzoate (Krigbaum & Barber, 1971)] and is of the same order as the N-O bonds in nitro groups or furoxans.…”

“…Henn. P. has been described (Gasco, Serafino, Mortarini, Menziani, Bianco & Ceruti Scurti, 1974) (9) S C(1) 1.493 (9) S C(2) 1.406 (9) C(1)-H(11) 1.01 (7) C(1)-H(12) 0.92 (6) C(1)-H(13) 1.300 (9) C(2)-H(21) 1.215 (8) C(2)-H(22) 1-11 (7) C(2)-H(23) 1-44 (7) 1 "499 (5) 1"761 (10) 1"756 (9) 0"85 (7) 1-05 (7) 0"84 (7) 1"09 (7) 1.01 (8) 0-92 (8)…”

Synthesis and Biological Evaluation of N2‐Substituted 2,4‐Diamino‐6‐cyclohexylmethoxy‐5‐nitrosopyrimidines and Related 5‐Cyano‐NNO‐azoxy Derivatives as Cyclin‐Dependent Kinase 2 (CDK2) Inhibitors

“…[7] This substance can be formally obtained by substitution of the nitroso group of 1 with the , which is present in the antibiotic "calvatic acid" (4-(Z)-cyano-NNO-azoxybenzoic acid) isolated for the first time from cultural broth of Calvatia lilacina. [8] . This unusual functional group has been used to design several bioactive compounds, such as antimicrobial and antitumor agents, enzyme inhibitors, and calcium channel blockers.…”

“…[7] This substance can be formally obtained by substitution of the nitroso group of 1 with the cyano-NNO-azoxy moiety,w hich is present in the antibiotic "calvatic acid" (4-[(Z)-cyano-NNO-azoxy]benzoic acid) initially isolated from the culture broth of Calvatia lilacina. [8] This unusual functional group has been used to design several bioactive compounds, such as antimicrobial and antitumor agents, enzyme inhibitors, andc alcium channel blockers. [9][10][11][12][13] The cyano-NNO-azoxy moiety displays an electron-withdrawing property very similar to that of the nitroso group (s pNO = 0.91, s pONNCN = 0.89), whereas it is endowed with different lipophilicity (p NO = À1.20, p ONNCN = À0.26) and steric properties.…”

The relationship between redox potentials and substituent constants in biologically active arylazoxy compounds

“…The cyanoazoxy group present in the antibiotic calvatic acid [4-(cyanoazoxy) benzoic acid, 1] [1,2] has been shown to be the pharmacophoric moiety, responsible for the antimicrobial and cytotoxic action of the antibiotic itself, as well as of a number of its analogues containing the cyanoazoxy function linked to various vectors [3][4][5][6][7][8].…”