2,4,6-Trinitrophenyl 4-bromobenzoate

Moreno-Fuquen, Rodolfo

doi:10.1107/s1600536813031061

Cited by 2 publications

(1 citation statement)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The latter was used as the starting material for one of the previously mentioned deviations from the main synthetic pathway. Unfortunately, our aim to obtain a set of dinitro esters crashed with the rather low stability of most such compounds . Uniquely, the benzoyl derivative 6 was obtained.…”

Section: Resultsmentioning

confidence: 99%

4-Hydroxy-3-nitro-5-ureido-benzenesulfonamides Selectively Target the Tumor-Associated Carbonic Anhydrase Isoforms IX and XII Showing Hypoxia-Enhanced Antiproliferative Profiles

et al. 2018

View full text Add to dashboard Cite

Human carbonic anhydrases (CA, EC, 4.2.1.1) IX and XII are overexpressed in cancer cells as adaptive response to hypoxia and acidic conditions characteristic of many tumors. In addition, hypoxia facilitates the activity of specific oxido-reductases that may be exploited to selectively activate bioreductive prodrugs. Here, new selective CA IX/XII inhibitors, as analogues of the antitumor phase II drug SLC-0111 are described, namely ureido-substituted benzenesulfonamides appended with a nitro-aromatic moiety to yield an antiproliferative action increased by hypoxia. These compounds were screened for the inhibition of the ubiquitous hCA I/II and the target hCA IX/XII. Six X-ray crystallographies with CA II and IX/mimic allowed for the rationalization of the compounds inhibitory activity. The effects of some such compounds on the viability of HT-29, MDA-MB-231, and PC-3 human cancer cell lines in both normoxic and hypoxic conditions were examined, providing the initiation toward the development of hypoxia-activated antitumor CAIs.

show abstract

Section: Resultsmentioning

confidence: 99%

4-Hydroxy-3-nitro-5-ureido-benzenesulfonamides Selectively Target the Tumor-Associated Carbonic Anhydrase Isoforms IX and XII Showing Hypoxia-Enhanced Antiproliferative Profiles

et al. 2018

View full text Add to dashboard Cite

show abstract

2,4,6-Trinitrophenyl 3-bromobenzoate

et al. 2014

Self Cite

View full text Add to dashboard Cite

In the title picryl-substituted ester, C13H6BrN3O8, the mean plane of the central ester C–O–C(=O)–C fragment (r.m.s. deviation= 0.0186 Å) is rotated by 84.73 (7)° and 19.92 (12)° to the picryl and phenyl rings, respectively. In the crystal, the molecules are linked by C—H⋯O interactions, forming centrosymmetric dimers enclosing R 2 2(10) and R 2 2(22) ring motifs along [001] and further helical chains of dimers enclosing R 2 2(10) ring motifs along [010].

show abstract

2,4,6-Trinitrophenyl 4-bromobenzoate

Cited by 2 publications

References 6 publications

4-Hydroxy-3-nitro-5-ureido-benzenesulfonamides Selectively Target the Tumor-Associated Carbonic Anhydrase Isoforms IX and XII Showing Hypoxia-Enhanced Antiproliferative Profiles

4-Hydroxy-3-nitro-5-ureido-benzenesulfonamides Selectively Target the Tumor-Associated Carbonic Anhydrase Isoforms IX and XII Showing Hypoxia-Enhanced Antiproliferative Profiles

2,4,6-Trinitrophenyl 3-bromobenzoate

Contact Info

Product

Resources

About