Synthesis and Antifungal Activity of Some New Quinazoline and Benzoxazinone Derivatives

Abstract

The hitherto unknown 2‐isopropyl‐6,8‐dibromo‐4H‐3,1‐benzoxazin‐4‐one (2) was subjected to condensation with either primary or secondary amines affording the benzamide derivatives (3—7), while with alcohols in presence of the base, corresponding esters were obtained (8 and 9). Acylation of the hydrazide (12) or its cyclized form (13) gave (14—17). The quinazolinone derivative (18) was obtained either when (12) was reacted with nitrous acid or via fusion of (2) with ammonium acetate. The thione (20) which was obtained via reaction of (18) with Lawesson's reagent, was subjected to either alkylation yielding (21—25) or desulphurization with primary amines affording (26 and 27). Treatment of (18) as well as (20) with a chlorinating agent provided (29, 30) and (28, 29) mixtures, respectively. Ten of our compounds were examined against Sclerotium cepivorum as well as Botrytis allii on PDA media. These compounds showed a significant reduction of mycelial growth and scleratia number of these fungi which cause the white rot and neck rot diseases of onion.

7-Nitro-2-phenyl-4H-3,1-benzoxazin-4-one

“…For related literature, see: Allen et al (1987); Bain & Smalley (1968); Bernstein et al (1995); Bouillant et al (1983); Colson et al (2005); El-Din (2000); Fenton et al (1989); Francis et al (2000); Gutschow et al (1998); Hamprecht et al (2004); Hauteville et al (1988); Hodson et al (2000); Johnson & Pattison (1986); Kakuta et al (2001); Krantz et al (1990); Mayama et al (1981); Pavlidis & Perry (1994); Ponchet et al (1984); Shalaby et al (2000); Ulrich (1991); Uejima et al (1993). Table 1 Hydrogen-bond geometry (Å , ).…”

“…Initial studies on 2-substituted-4H-3,1-benzoxazin-4-one showed good cytotoxic activity (Pavlidis & Perry, 1994) and herbicidal properties (Hamprecht et al, 2004). A variety of biological activities were associated with 2-Substituted-4H-3,1-benzoxazin-4-ones for example antifungal, antibacterial (Bouillant et al, 1983;Ponchet et al, 1984;Mayama et al, 1981;Hauteville et al, 1988;El-Din, 2000;Shalaby et al, 2000) and anti-elastase properties (Colson et al, 2005). They can be used for the treatment of obesity (Hodson et al, 2000) and also found to be novel specific puromycin-sensitive aminopeptidase inhibitors (Kakuta et al, 2001).…”

2-Alkyl(aryl)-quinazolin-4(3H)-thiones, 2-R-(quinazolin-4(3H)-ylthio)carboxylic acids and amides: synthesis, molecular docking, antimicrobial and anticancer properties

“…The 4-ethylthio-6-fluoroquinazoline had potent antifungal activities against practically all the tested fungi (Gibberella zeae, Fusarium oxysporum, Cardamine mandshurica, Rhizoctonia solani, Thanatephorus cucumeris, Phytophthora infestans, Sclerotinia sclerotiorum, Botrytis cinerea, Colletotrichum gloeosporioides) and showed a broad-spectrum bioactivity 9 . Also quinazoline-4(3H)-thione's derivatives possessed antifungal properties against Sclerotium cepivorum and Botrytis allii 10 . Even bis-quinazolines showed antimicrobial activity 11 .…”

A facile and efficient synthesis of 4H-1,3-benzoxazine-4-one with electron-withdrawing group derivatives

“…1 Particularly, benzoxazine derivatives display various biological activities such as anticancer, 2 antimicrobial, 3 antifungal, 4 and antiplatete 5 activities. As part of an ongoing medicinal chemistry program on anti-tuberculosis drug discovery, 1,3-benzoxazin-4-one motif has attracted our considerable interest.…”