Utilization of Dipotassium Salt of Galactaric Acid Bis(Hydrazidocarbodithioic Acid) As a Synthone for Double-Headed 1,3,4-Thiadiazoline, 1,3,4-Oxadiazoline and 1,2,4-Triazoline Acyclo C-Nucleosides

Double-headed nucleosides: Synthesis and applications

“…The acyclic double-headed nucleosides 232a and 233-235 were screened for their in vitro antibacterial activity against the Gram-negative bacterium Escherichia coli and the Gram-positive bacterium Staphylococcus aureus and for their antifungal activity against Candida albicans using the agar diffusion method [103]. Among the tested compound, derivative 235 showed fair activity against E. coli and C. albicans but was inactive against S. aureus whereas compound 234 showed activity only against S. aureus [19]. Amara and Othman [20] synthesized the double-headed acyclo-C-nucleosides 1,4-bis(3-mercapto-1H-1,2,4-triazol-5-yl)butane- The double-headed C-nucleosides 240-242 were tested in vitro against Gram-positive bacteria Staphylococcus aureus, Listeria inovanii and Gram-negative bacteria Klebsiella pneumoniae, Salmonella sp., and Escherichia coli.…”

“…Nasr and co-workers [ 19 ] also synthesized double-headed 1,2,4-triazoline ( 232a,b , 233 ), 1,3,4-oxadiazoline ( 234 ), 1,3,4-thiadiazoline ( 235 ) acyclo C -nucleosides starting from galactaric acid hydrazide ( 215 ). The syntheses started with the condensation of compound 215 with carbon disulfide in the presence of ethanolic potassium hydroxide to give the dipotassium salt of galactaric acid bis(hydrazidocarbodithioic acid) which was then heterocyclized under different reaction conditions to give three types of double-headed nucleosides ( Scheme 62 ) [ 19 ].…”

“…The acyclic double-headed nucleosides 232a and 233–235 were screened for their in vitro antibacterial activity against the Gram-negative bacterium Escherichia coli and the Gram-positive bacterium Staphylococcus aureus and for their antifungal activity against Candida albicans using the agar diffusion method [ 103 ]. Among the tested compound, derivative 235 showed fair activity against E. coli and C. albicans but was inactive against S. aureus whereas compound 234 showed activity only against S. aureus [ 19 ].…”

“…On the other hand, a variety of heterocyclic/carbocyclic moieties were considered as the head of these modified nucleosides. The heterocyclic structures which were found to be attached to these double-headed nucleosides include triazolophthalazine [11], 4,6-di-tert-butylbenzoxazole [12], mesitylisoxazole [13], 5-trimethylsilyl-1,2,3-triazole [14], 1-pivaloyloxymethyl-1H-1,2,3-triazole [15], 1,3,4-oxadiazino [6,5-b]indole [16], 6,7-dihydro-6-oxo-5H-1,2,4triazolo [3,4-b][1, 3,4]thiadiazine [17], 1,2,4-triazino [5,6b]indole [18], 1,3,4-thiadiazoline [19], 1,3,4-oxadiazoline [19], 1,2,4-triazoline [19], 3-mercapto-1H-1,2,4-triazole [20], 1,3,4oxadiazole-2(3H)-thione [20], 4-amino-5-mercapto-4H-1,2,4triazole [20], and 1,2,4-triazolo [3,4-b](1,3,4)-thiadiazole moieties [21]. Additionally, selected examples of doubleheaded nucleosides comprising aromatic/polyaromatic/carbocyclic moieties such as phenyl [13][14][15]22], pyrene [23][24][25], adamant-1-yl [24], cholesteryl [24], perylen-3-yl [24], 4-(tertbutyldimethylsilyloxy/hydroxy)phenyl [26], 3/4-(N-((dimethylamino)methy-lidene)aminosulfonyl)phenyl [26,27], and sulfonamido-substituted benzothiazole [28] attached as an additional head are also reported in this review article.…”

Isolation, characterization, anticancer and antioxidant activities of 2-methoxy mucic acid from Rhizophora apiculata: An in vitro and in silico studies

“…In this regard, the mucic acid has been used as a versatile intermediate for the synthesis of various natural products as well as pharmaceutical drugs such as pyrones (Leonardi et al, 2020), pectin derived galacturonic acid (Purushothaman et al, 2018), furan and its polyester (Zhao et al, 2019), salts of mucic acid (Tian et al, 2000), adipic acid (Li et al, 2014), mucic acid 1,4-lactone methyl ester 3-O-ferulate (Sengoku et al, 2012) and mucic acid polymer products (Pan et al, 2015). In addition to mucic acid, its derivatives have exhibited various biological properties such as antioxidant (Luo et al, 2011;Olennikov et al, 2015), antimicrobial (Nasr and Mostafa, 2005), anticancer (Luo et al, 2011;Zhang et al, 2017) and antidiabetic activities (Patel and Goyal, 2011).…”