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97-09-6

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97-09-6 Usage

Uses

4-Chloro-3-nitrobenzenesulfonamide is used as a chemical intermediate for azo dyes.

Synthesis

Chlorosulphonic acid (450 mL) was slowly added to 2-chloronitrobenzene (100 g). The reaction mass was heated to 100°C and maintained at that temperat ure for 6 hours before cooling to ambient temperature and stirring for an additional 12 hours. The reaction mass was slowly poured into chilled aqueous ammonia (800 mL) and the reaction mixture was stirred for 3 hours at -10°C. The reaction mixture was then warmed to 23°C and stirred for 2 h ours. The reaction mixture was then filtered and the obtained solid was washed three times with water (200 mL x 3). The solid was dissolved in methanol (600 mL) at 60°C, charged with water (200 mL), and was stirred for 1 hour at 60°C. Again, the reaction mixture was charged with water (200 mL) and stirred for 1 hour at 60°C. Once again, the reaction mixtu re was charged with water (200 mL) and stirred for 1 hour. After cooling to room temperature and stirring for 1 hour, the reaction mixture was filtered, and the solid was washed with a 1 :1 mixture of methanol and water (100 mL). The solid was dried under vacuum at 60°C. Crystallization of the residue with toluen e gave the 4-Chloro-3-nitrobenzenesulfonamide(50 g).

Check Digit Verification of cas no

The CAS Registry Mumber 97-09-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 7 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 97-09:
(4*9)+(3*7)+(2*0)+(1*9)=66
66 % 10 = 6
So 97-09-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H5ClN2O4S/c7-5-2-1-4(14(8,12)13)3-6(5)9(10)11/h1-3H,(H2,8,12,13)

97-09-6Relevant articles and documents

Benzimidazole derivatives as potent and isoform selective tumor-associated carbonic anhydrase IX/XII inhibitors

?al??kan, Burcu,Banoglu, Erden,Gür Maz, Tu??e,Nocentini, Alessio,Supuran, Claudiu T.,Uslu, Azize Gizem

supporting information, (2020/01/08)

We describe the synthesis of a series of 2-arylbenzimidazole derivatives bearing sulfonamide functionality (4a–d, 7a–c and 10) as well as hydroxamic acid (15a–b), carboxylic acid (16a–b), carboxamide (17a–b) and boronic acid (22a–b and 26) functionalities, which act as human carbonic anhydrase (hCA, EC 4.2.1.1) inhibitors. The newly synthesized benzimidazole derivatives were evaluated against 4 physiologically relevant CA isoforms (hCA I, II, IX, and XII), and especially the sulfonamide-containing benzimidazoles demonstrated intriguing inhibitory activity against tumor associated CA IX and XII with KI values in the range of 5.2–29.3 nM and 9.9–41.7 nM, respectively. Notably, compound 4c was the most potent and selective CA IX (KI = 6.6 nM) and XII (KI = 9.9 nM) inhibitor with a significant selectivity ratio over cytosolic CA I and II isoforms in the range of 3.4–25.2. In addition, compounds having hydroxamic acid (15a-b) or carboxylic acid (16a-b) functionalities resulted in greater selectivity ratios for CA IX/XII over CAI/II in the range of 4.1–121.5 although with KI values in lower micromolar potency (KIs = 0.36–0.85 μM for CA IX/XII).

PROCESS FOR THE PREPARATION OF VENETOCLAX

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Page/Page column 30; 31, (2018/03/06)

The present disclosure provides novel synthetic process for the preparation of venetoclax. The disclosed processes involve the use of novel intermediates. Processes for the preparation of these intermediates are also disclosed as well as methods for the preparation of particularly useful salts thereof.

Discovery of a potent inhibitor of the antiapoptotic protein Bcl-X L from NMR and parallel synthesis

Petros, Andrew M.,Dinges, Jurgen,Augeri, David J.,Baumeister, Steven A.,Betebenner, David A.,Bures, Mark G.,Elmore, Steven W.,Hajduk, Philip J.,Joseph, Mary K.,Landis, Shelley K.,Nettesheim, David G.,Rosenberg, Saul H.,Shen, Wang,Thomas, Sheela,Wang, Xilu,Zanze, Irini,Zhang, Haichao,Fesik, Stephen W.

, p. 656 - 663 (2007/10/03)

The antiapoptotic proteins Bcl-xL and Bcl-2 play key roles in the maintenance of normal cellular homeostasis. However, their overexpression can lead to oncogenic transformation and is responsible for drug resistance in certain types of cancer. This makes Bcl-xL, and Bcl-2 attractive targets for the development of potential anticancer agents, Here we describe the structure-based discovery of a potent Bcl-xL inhibitor directed at a hydrophobic groove on the surface of the protein. This groove represents the binding site for BH3 peptides from proapoptotic Bcl-2 family members such as Bak and Bad. Application of NMR-based screening yielded an initial biaryl acid with an affinity (Kd) of ~300 μM for the protein. Following the classical "SAR by NMR" approach, a second-site ligand was identified that bound proximal to the first-site ligand in the hydrophobic groove. From NMR-based structural studies and parallel synthesis, a potent ligand was obtained, which binds to Bcl-xL with an inhibition constant (K i) of 36 ± 2 nM.

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