English (United Kingdom)

https://curated-unify.zendy.io/wp-json/zendy-region/v1/featured_content/oa?rat=en

https://curated-unify.zendy.io/wp-json/zendy-region/v1/highlighted_journal/

Global: Zendy Tools annual

Presents the keyphrase highlighting as premium feature

Keyphrase Highlighting

Presents the summarisation as premium feature

Summarisation

Insights

Presents the pdf analysis as premium feature

PDF Analysis

Presents the zaia usage as premium feature

ZAIA

Global: Zendy Tools monthly

Global: Zendy Plus monthly

Presents the access of premium content as premium feature

Premium Content

Global: Zendy Plus annual

Global: Zendy Free Plan

l,8-Bis[(3-aryl)-s-triazolo[3,4-ft]-[l,3,4]thiadiazole-6-yl]octanes 2 were synthesized in high yields by reaction of 3-aryl 4-amino-5-mercapto-l,2,4-triazole 1 with sebacic acid in the presence of P0C13 and tetrabutylammonium iodide as catalyst. The structures have been established on the basis of elemental analysis and spectral date. The preliminary antibacterial tests showed that most of them were effective against S.aureus, E.coli and B.subtilis. 2b, 2c, 2d, 2n and 2o exhibited good fungicidal activities against Cerospora beticola sacc. Introduction Bis[l,2,4-Bis[l,2,4-triazolo[3,4-ö]-[l,3,4]thiadiazole-4-yl]alkanes were reported to possess antibacterial property (l)and bis[l,2,4-triazolo[3,4-6]-[l,3,4]thiadiazol-3-yl-meth -oxy]phenylenes possess anticancer activity against a panel of 60 cell lines derived from seven cancer types namely, lung, colon, melanoma, renal, ovarian, and leukemia (2). 2,5-Bis[(3-aryl)-l,2,4-triazolo[3,4-ö]-[l,3,4]thiadiazole-6-yl]pyridines (3) and 2,6-Bis [(3-aryl)-l,2,4-triazolo[3,4-0]-[l,3,4]thiadiazole-6-yl]pyridines (4) endowed with good fungicidal activities against Cerospora beticola sacc have been reported from our laboratory. l,4-Bis[(3-aiyl)-l,2,4-triazolo[3,4-6]-[l,3,4] thiadiazole-6-yl]butanes (5) and trans-l,2-bis[(3-aryl)-l,2,4-triazolo[3,4-6]-[l,3,4] thiadiazole-6-yl]ethenes (6) were found to show significant antibacterial activities. Prompted by these observation and in continuation of our search for bio-active molecules, We designed a facile one-pot method to prepare fifteen new l,8-bis[(3-aryl)-striazolo[3,4-6]-[l,3,4]thiadiazole-6-yl]octanes by cyclization of 3-aryl-4-amino-5-mercapto-l,2,4-triazoles with octanedioic acid. The synthesis, characterization and the results of antibacterial and fungicidal activities screening studies of the newly synthesized compounds are presented in this paper. Result and Discussion The synthesis of l,8-bis[(3-aryl)-s-triazolo[3,4-6]-[l,3,4]thiadiazole-6-yl]octanes 2 was accomplished in one step with good yields by condensing 3-aryl-4-amino-5mercapto-l,2,4-triazoles 1 with sebacic acid in the presence of POCI3 and tetrabutylammonium iodide as catalyst (Scheme 1, Table 1). Because of the poor solubility of 1 and sebacic acid in POCI3, the yield of 2 is very low. For example, the yield of 2a was 30%. However, where the tetrabutylammonium iodide as phase transfer catalyst were utilized and the mixture was first stirred for 4 h at 55-60 °C, then refluxed for 9-11 h at 69 Unauthenticated Download Date | 6/1/19 10:42 PM Vol. 14, Nos. 1-2, 2008 Antibacterial andfungicidal activities of 1,8-bis 115-120 °C, 2a was obtained in 80% yield. HOOC-(CH2)8-COOH + Ar N-N SH (n-C4H9)4NI POCb _ Ai N-N h \ Ν \ Ν N N // \\ -Ar 7 -Ν NH2 1 2 Scheme 1 Table 1 : Preparation of l,8-Bis[(3-aryl)-s-triazolo[3,4-6]-[l,3,4]thiadiazole-6-yl]octanes 2 from 3-aryl-4-amino-5-mercapto-l, 2, 4-triazoles 1. Entry Ar Condition Yield(%) m.p.(°C) 2a Ph 115-120°C/9.0h 80 >250 2b 2-C1-PH 115-120°C/9h 70 207-209 2c 3-Cl-Ph 115-120*0/1 Oh 65 204-207 2d 4-Cl-Ph 115-120°C/1 lh 72 210-208 2e 2 C H r P h 115-120°C/10h 68 189-187 I t 3-CH3-Ph 115-120*0/1 Oh 71 194-192 2g 4-CH3-Ph 115-120°C/9h 74 202-201 2h 3-Br-Ph 115-120°C/9h 65 216-218 2i 4-Br-Ph 115-120°C/10h 71 212-210 2j 2-I-Ph 115-120°C/1 lh 58 207-209 2k 3-I-Ph 115-120*0/1 Oh 65 219-221 21 4-I-Ph 115-120°C/11 h 77 213-215 2m 4-OCH3-Ph 115-120°C/13h 72 1 9 7 1 9 9 2n 4-Pyridyl 115-120°C/10h 60 >250 2o 3-Pyridyl 115-120*0/1 lh 65 >250 "Purified yields of 2a-2o based on sebacic acid. The structures of all compounds 2 were established on the basis of elemental analysis and spectral data. The IR spectral data of compounds 2 showed bands at 1620-1645 cm", 1235-1260 cm", and 700-710 cm" due to C=N, N-N=C and C-S-C, respectively. The *Η NMR spectra of 2 exhibited multiple signals in the δ 8.90-7.30 range accounting for hydrogen of aryl group, a triplet at δ 3.20 accounting for the 4 hydrogens of -2SCH2, 2.05-1.85 range accounting for the 4 hydrogens of -2SCH?CH?, 1.60-1.45 range attributing to the 8 hydrogens of CH2CH2CH2CH2. With compound 2a as an example, it exhibited multiple signals in the δ 8.33-8.30, 7.81-7.58 ranges accounting for the 10 hydrogens of phenyl groups, a triplet at δ 3.29 accounting for the 4 hydrogens of -2SCH2, a multiple signals at δ 2.01 -1.98 attributing to the 4 hydrogens of2SCH?CH?, a multiple signals in the 70 Unauthenticated Download Date | 6/1/19 10:42 PM Li et al. Heterocyclic Communications δ 1.58-1.49 ranges accounting for the 8 hydrogens of CH2CH2CH2CH2. The ΕΙ-MS for compounds 2 exhibited molecular ion peaks. For example, 2a showed strong molecular ion peak M with m/z 514 and 11% relative abundance. Compounds 2 were screened for their antibacterial activities against E. coli, S. aureus, and B. subtilis employing the cup-plate method at the concentration of 100 μg/mL in the nutrient agar. The preliminary results indicated that most of compounds express significant antibacterial activity. The results of such studies are given in table 2. The biological 70 ities of compounds 2 were investigated and the results showed that they exhibited fungicidal activities, especially against Cerospora beticola sacc. For example, 2b, 2c, 2d, 2n and 2o showed 92% of Cerospora beticola sacc inhibition of in 50 mg/L (see Table 3). Table 2 The Antibacterial Activities of Compounds 2a-3o Compd. S. aureus E.coli B. subtilis 2a + + + 2b + + + + + + + 2c + + + + + + + + 2d + + + + + + + + 2e + +

ANTIBACTERIAL AND FUNGICIDAL ACTIVITIES OF 1,8-BIS[(3-ARYL)-S-TRI AZOLO [3,4-B] - [1,3,4]THIADIAZOLE-6-YL] OCTANES