New nonsteroidal antiinflammatory agent. 3. Analogs of 2-substituted 5-benzothiazoleacetic acids and their derivatives

Miyamatsu, Hiroki; Ueno, Shinji; Shimizu, Mitsuhiro; Hosono, Jinichi; Tomari, Masazumi; Seida, Keiichi; Suzuki, Tadayuki; Wada, Jin

doi:10.1021/jm00251a004

Cited by 14 publications

(5 citation statements)

References 10 publications

(15 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Anal. (Ci7Hi6C1N202) C, , N. 5-(l-phenylethyl)barbituric acids (2)(3)(4)(5) were prepared by alkylation of 5-propionoxy-5-(l-phenylethyl)barbituric acid (1) with alkyl chloromethyl ethers in the presence of 2 equiv of base. 1,3-Bis (acetoxymethyl) -5-propionoxy-5-(1 -phenylethyl)barbituric acid (6) was prepared from 1 and bromomethyl acetate in a similar manner.…”

Section: -mentioning

confidence: 99%

Synthesis and antiinflammatory activity of some 2-substituted .alpha.-methyl-5-benzimidazoleacetic acids

Dunwell¹,

Evans²,

Smith³

et al. 1975

J. Med. Chem.

View full text Add to dashboard Cite

show abstract

Section: -mentioning

confidence: 99%

Synthesis and antiinflammatory activity of some 2-substituted .alpha.-methyl-5-benzimidazoleacetic acids

Dunwell¹,

Evans²,

Smith³

et al. 1975

J. Med. Chem.

View full text Add to dashboard Cite

show abstract

“…Various substituted benzothiazoles are known to possess a wide range of pharmacological activities such as antitumour [12], antimicrobial [13,14], anthelmintic [15], analgesic [16], anti-inflammatory [17] and anticonvulsant [18] activities. Similarly, the ß-lactam nucleus is considered a general lead structure for the design and synthesis of not only new antibacterial products, but also for new inhibitors of enzymes like ß-lactamases [19], human leukocyte elastase [20], cholesterol absorption inhibitors [21] and human cytomegalovirus protease [22].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti-inflammatory Activity of Alkyl/Arylidene-2-aminobenzothiazoles and 1-Benzothiazol-2-yl-3-chloro-4-substituted-azetidin-2-ones

Khedekar¹,

Bahekar

Chopade

et al. 2011

Arzneimittelforschung

View full text Add to dashboard Cite

Ten new derivatives of 1-benzothiazol-2-yl-3-chloro-4-substituted-azetidin-2-ones (3a-j) were synthesized using various Schiff bases (alkyl/arylidene-2-aminobenzothiazoles; 2a-j), which in turn were prepared starting from 2-aminobenzothiazole (1). All the synthesised compounds were characterised by elemental analyses and spectral (IR, 1H-NMR, 13C-NMR and EI-MS) data. The title compounds 2a-j and 3a-j were screened in vivo using carrageenan-induced rat paw edema model. All the test compounds showed anti-inflammatory activity when tested in vivo. In general, compounds 3a-j were found to be more potent compared to compounds 2a-j. Among the compounds tested, compound 2g in the alkyl/arylidene-2-aminobenzothiazoles series and compound 3 g in the 1-benzothiazol-2-yl-3-chloro-4-substituted-azetidin-2-ones series were found to be the most potent. All the test compounds were also evaluated to check the gastric ulcer incidence. In gastric ulceration studies, all the test compounds were generally found to be safe at the 100 mg/kg dose level. Furthermore the most potent compounds 2 g and 3 g from each series were screened in vitro for inhibition of both COX-2 and COX-1 catalysed prostaglandin biosynthesis (radiochemical assay). Like most of the commercially available non-steroidal anti-inflammatory drugs (NSAIDs), in the in vitro study, compounds 2 g and 3 g showed anti-inflammatory activity by blocking the metabolism of arachidonic acid to prostaglandin via the cyclooxygenase pathways. In general, in the vitro assay, test compounds 2 g and 3 g were found to be more active after 15 min pre-incubation with the enzyme. Compound 3 g was found to be more COX-2 selective, while compound 2 g was found to be equally COX-2 and COX-1 selective.

show abstract

“…The progress in the studies of rutaecarpine has been reviewed [8]. Recently numerous thiophene analogues of rutaecarpine [9] as well as quinazoline have shown good anticancer activity [10], analgesic [11], anti-inflammatory [12][13][14] as well as antiparkinsonims activity [15]. Bioisosterism is a strategy of medicinal chemistry for the rational design of new drug, applied with a lead compound as a special process of molecular modification [16].…”

Section: Introductionmentioning

confidence: 99%

The Synergy of Combined Use of DMSO and Bronsted Acid (Ionic Liquid) as a Catalyst Part I: Efficient Niementowski Synthesis of Modified Quinazolinones

Kathiravan¹,

Jalnapurkar²,

Chitre³

et al. 2011

GSC

View full text Add to dashboard Cite

A new rapid and versatile approach using Ionic liquid/DMSO as a chemical reagent for the synthesis of fused heterocyclic compounds in a highly efficient way is described. This method offers the advantages of proceeding in neutral conditions, giving high to excellent isolated yields (83–92%) for Niementowski synthesis with easy workup procedure. The inherent Bronsted acidity of ionic liquid and high polarity of both IL and DMSO resulted in a significant enhancement in the reaction rate

show abstract

New nonsteroidal antiinflammatory agent. 3. Analogs of 2-substituted 5-benzothiazoleacetic acids and their derivatives

Cited by 14 publications

References 10 publications

Synthesis and antiinflammatory activity of some 2-substituted .alpha.-methyl-5-benzimidazoleacetic acids

Synthesis and antiinflammatory activity of some 2-substituted .alpha.-methyl-5-benzimidazoleacetic acids

Synthesis and Anti-inflammatory Activity of Alkyl/Arylidene-2-aminobenzothiazoles and 1-Benzothiazol-2-yl-3-chloro-4-substituted-azetidin-2-ones

The Synergy of Combined Use of DMSO and Bronsted Acid (Ionic Liquid) as a Catalyst Part I: Efficient Niementowski Synthesis of Modified Quinazolinones

Contact Info

Product

Resources

About