Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalosporanic acid

Kukolja, Stjepan; Draheim, Susan E.; Graves, Bernard J.; Hunden, David C.; Pfeil, J. L.; Cooper, R. D. G.; Ott, J. L.; Counter, F. T.

doi:10.1021/jm00150a023

Cited by 40 publications

(19 citation statements)

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“…Thieno [2,3-b]thiophene compounds have been developed for different target, in the medicinal field and have been tested as prospect antitumor, antiviral, antibiotic, and antiglaucoma drugs, or as inhibitors of lamina series [1][2][3][4][5].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1,1,(3,4-dihydroxythieno[2,3-b] thiophene-2,5-diyl)bis(2-bromoethanone), C₁₀H₆Br₂O₄S₂

Mabkhot

Al-aizari

Al–Showiman

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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C 10 H 6 Br 2 O4S 2 , monoclinic, P21/c (no. 14), a = 8.1199 ( CCDC no.: 1486828The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters. (100 mL) was heated to 90-100°C with stirring. To this hot solution, bromine (1.6 g, 10 mmol) in acetic acid (20 mL) was added dropwise over a period of 40 min. After complete addition of bromine, the reaction mixture was stirred vigorously at room temperature for further 1 h, then it was poured onto cold water. The solid that formed was collected, washed with water, dried and recrystallized from ethanol to give colorless crystals of the title compound.; yield 40%, mp. 120°C; Source of material Experimental detailsCarbon-bound H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with U iso (H) set to 1.2Ueq(C). The H atoms of the hydroxyl groups were allowed to rotate with a fixed angle around the C-O bond to best fit the experimental electron density (HFIX 147 [12]), with U iso (H) set to 1.5Ueq(O). DiscussionThieno [2,3-b]thiophene compounds have been developed for different target, in the medicinal field and have been

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Section: Discussionmentioning

confidence: 99%

Crystal structure of 1,1,(3,4-dihydroxythieno[2,3-b] thiophene-2,5-diyl)bis(2-bromoethanone), C₁₀H₆Br₂O₄S₂

Mabkhot

Al-aizari

Al–Showiman

et al. 2017

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Thienothiophene derivatives have been reported to exhibit awide variety of pharmacological effects, including antitumor, antiviral, antibiotic, and antiglaucomap roperties, or as inhibitors of platelet aggregation [4][5][6][7][8]. Some thieno [2,3-b]thiophene derivatives also inhibit several important enzymes in cellular systems, such as a-glucosidase and b-glucuronidase inhibition, or exhibited DPPH radical scavenging antioxidant activity [9][10].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 1-(5-acetyl-3,4-dimethyl-thieno[2,3-b]thiophen-2-yl)- ethanone, C12H12O2S2

Mabkhot¹,

Al‐Majid²,

Barakat³

et al. 2014

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Thieno [3,2-d]pyrimidine derivatives display a wide range of activities acting as anticonvulsants (9), antivirals (10), antibiotics (11), antiglaucoma agents (12) and platelet aggregation inhibitors (13). On the other hand, some 2-substituted-thieno [3,2-d]pyrimidine--4-ones are considered to exert antihyperlipidemic (14) and anti-inflammatory activity (15).…”

Section: Abstract: Thieno[32-d]pyrimidines Thienotriazolopyrimidinementioning

confidence: 99%

“…The solid obtained after evaporation of the solvent was filtered off, dried and recrystallized from dioxane. (11). -A mixture of 2 (0.01 mol) and hydrazine hydrate (99 %) (25 mL) was stirred under gentle reflux.…”

Section: -(Alkoxyphenoxy)-3-methyl-6-phenyl-thieno[32-d]pyrimidine-mentioning

confidence: 99%

Synthesis and evaluation of antitumor activity of new 4-substituted thieno[3,2-d]pyrimidine and thienotriazolopyrimidine derivatives

Hafez

El‐Gazzar

2017

Acta Pharmaceutica

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3-Methyl-6-phenyl-2-thioxo-2,3-dihydrothieno[3,2-d]pyrimidin- 4(1H)-one (2), on treatment with phosphorous oxychoride, affored 4-chloro-3-methyl-6-phenyl -thieno[3,2-d]pyrimidine- 2(3H)-thione (3). A series of novel 6-phenyl-thieno[3,2-d]pyrimidine derivatives 4-9 bearing different functional groups were synthesized via treatment of compound 3 with different reagents. On the other hand, compound 2 was used to synthesize ethyl-[(3-methyl-6-phenyl-2-thioxo-2,3-dihydrothieno[ 3,2-d]pyrimidin-4-yl)-oxy]acetate (10), 2-hydrazinyl- -3-methyl-6-phenyl-thieno[3,2-d]pyrimidin-4(3H)-one (11), 3-methyl-2-(methyl-sulfanyl)-6-phenyl-thieno[3,2-d]pyrimidin- 4(3H)-one (12) and N-(phenyl)/4-chlorophenyl or methoxy- phenyl)-2-[(3-methyl-4-oxo-6-phenyl-3,4-dihydrothieno[ 3,2-d]pyrimidin-2-yl)-sulfanyl]-acetamide (13a-c). In addition, compound 12 was used to synthesize thieno[1,2,4] triazolopyrimidine derivatives 14 and 15 and 3-methyl-2-(methyl-sulfonyl)-6-phenyl-thieno[3,2-d]pyrimidin-4(3H)-one (16) through the reaction with the respective reagents. Moreover, the reaction of 16 with 4-phenylenediamine gave 2-[(4-aminophenyl)-amino]-3-methyl-6-phenyl-thieno[3,2-d] pyrimidin-4(3H)-one (17), which reacted with methanesulfonyl chloride to afford N-{4-[(3-methyl-4-oxo-6-phenyl-3H,4H- -thieno[3,2-d]pyrimidin-2-yl)-amino]phenyl}-methanesulfonamide (18). The majority of the newly synthesized compounds displayed potent anticancer activity, comparable to that of doxorubicin, on three human cancer cell lines, including the human breast adenocarcinoma cell line (MCF-7), cervical carcinoma cell line (HeLa) and colonic carcinoma cell line (HCT- 116). Compounds 18, 13b and 10 were nearly as active as doxorubicin whereas compounds 6, 7b and 15 exhibited marked growth inhibition, but still lower than doxorubicin.

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Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalosporanic acid

Cited by 40 publications

References 0 publications

Crystal structure of 1,1,(3,4-dihydroxythieno[2,3-b] thiophene-2,5-diyl)bis(2-bromoethanone), C₁₀H₆Br₂O₄S₂

Crystal structure of 1,1,(3,4-dihydroxythieno[2,3-b] thiophene-2,5-diyl)bis(2-bromoethanone), C₁₀H₆Br₂O₄S₂

Crystal structure of 1-(5-acetyl-3,4-dimethyl-thieno[2,3-b]thiophen-2-yl)- ethanone, C12H12O2S2

Synthesis and evaluation of antitumor activity of new 4-substituted thieno[3,2-d]pyrimidine and thienotriazolopyrimidine derivatives

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Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalosporanic acid

Cited by 40 publications

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Crystal structure of 1,1,(3,4-dihydroxythieno[2,3-b] thiophene-2,5-diyl)bis(2-bromoethanone), C10H6Br2O4S2

Crystal structure of 1,1,(3,4-dihydroxythieno[2,3-b] thiophene-2,5-diyl)bis(2-bromoethanone), C10H6Br2O4S2

Crystal structure of 1-(5-acetyl-3,4-dimethyl-thieno[2,3-b]thiophen-2-yl)- ethanone, C12H12O2S2

Synthesis and evaluation of antitumor activity of new 4-substituted thieno[3,2-d]pyrimidine and thienotriazolopyrimidine derivatives

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Crystal structure of 1,1,(3,4-dihydroxythieno[2,3-b] thiophene-2,5-diyl)bis(2-bromoethanone), C₁₀H₆Br₂O₄S₂

Crystal structure of 1,1,(3,4-dihydroxythieno[2,3-b] thiophene-2,5-diyl)bis(2-bromoethanone), C₁₀H₆Br₂O₄S₂