tosyl compounds

Summary

Summary: Toluenesulfonyl compounds with general formula CH3C6H4S(O2)R” widely used to block amino groups in the course of syntheses of drugs and other biologically active compounds.

Top Publications

  1. Ishikura N, Kawata H, Nishimoto A, Nakamura R, Ishii N, Aoki Y. Establishment and characterization of an androgen receptor-dependent, androgen-independent human prostate cancer cell line, LNCaP-CS10. Prostate. 2010;70:457-66 pubmed publisher
  2. Lin T, Lee S, Niu Y, Xu D, Liang L, Li L, et al. Differential androgen deprivation therapies with anti-androgens casodex/bicalutamide or MDV3100/Enzalutamide versus anti-androgen receptor ASC-J9(R) Lead to promotion versus suppression of prostate cancer metastasis. J Biol Chem. 2013;288:19359-69 pubmed publisher
    ..These findings suggest the potential risks of using anti-androgens and provide a potential new therapy using ASC-J9® to battle PCa metastasis at the castration-resistant stage. ..
  3. Kawata H, Ishikura N, Watanabe M, Nishimoto A, Tsunenari T, Aoki Y. Prolonged treatment with bicalutamide induces androgen receptor overexpression and androgen hypersensitivity. Prostate. 2010;70:745-54 pubmed publisher
    ..However, the mechanism of bicalutamide resistance remains unclear because few cell models have been generated...
  4. Ni M, Chen Y, Lim E, Wimberly H, Bailey S, Imai Y, et al. Targeting androgen receptor in estrogen receptor-negative breast cancer. Cancer Cell. 2011;20:119-31 pubmed publisher
    ..Specific targeting of AR, Wnt or HER2 signaling impairs androgen-stimulated tumor cell growth suggesting potential therapeutic approaches for ER-/HER2+ breast cancers...
  5. Tran C, Ouk S, Clegg N, Chen Y, Watson P, Arora V, et al. Development of a second-generation antiandrogen for treatment of advanced prostate cancer. Science. 2009;324:787-90 pubmed publisher
    ..These compounds thus appear to be promising candidates for treatment of advanced prostate cancer...
  6. Jin F, Fondell J. A novel androgen receptor-binding element modulates Cdc6 transcription in prostate cancer cells during cell-cycle progression. Nucleic Acids Res. 2009;37:4826-38 pubmed publisher
    ..Collectively, our results suggest that Cdc6 is a key regulatory target for AR and provide new insights into the mechanisms of prostate cancer cell proliferation...
  7. Kim S, Richardson M, Chinnakannu K, Bai V, Menon M, Barrack E, et al. Androgen receptor interacts with telomeric proteins in prostate cancer cells. J Biol Chem. 2010;285:10472-6 pubmed publisher
    ..Together, these observations suggest an allosteric role of AR in telomere complex stability in prostate cancer cells and suggest that AR-antagonist Casodex-mediated cell death may be due to telomere complex disruption...
  8. Alonzi R, Padhani A, Taylor N, Collins D, d Arcy J, Stirling J, et al. Antivascular effects of neoadjuvant androgen deprivation for prostate cancer: an in vivo human study using susceptibility and relaxivity dynamic MRI. Int J Radiat Oncol Biol Phys. 2011;80:721-7 pubmed publisher
  9. Zaharia V, Ignat A, Palibroda N, Ngameni B, Kuete V, Fokunang C, et al. Synthesis of some p-toluenesulfonyl-hydrazinothiazoles and hydrazino-bis-thiazoles and their anticancer activity. Eur J Med Chem. 2010;45:5080-5 pubmed publisher
    ..Compounds 2a, 2c, 2d, 2e and 3a showed significant anticancer activities (IC(50)<10 ?M) on both prostate DU-145 and hepatocarcinoma Hep-G2 cancer cell lines. ..

More Information

Publications62

  1. Quero L, Giocanti N, Hennequin C, Favaudon V. Antagonistic interaction between bicalutamide (Casodex) and radiation in androgen-positive prostate cancer LNCaP cells. Prostate. 2010;70:401-11 pubmed publisher
    ..However, biological data for the interaction between bicalutamide and ionizing radiation in concomitant association are lacking...
  2. Akaza H. Combined androgen blockade for prostate cancer: review of efficacy, safety and cost-effectiveness. Cancer Sci. 2011;102:51-6 pubmed publisher
  3. Jayaram L, Chunilal S, Pickering S, Ruffin R, Zalewski P. Sputum zinc concentration and clinical outcome in older asthmatics. Respirology. 2011;16:459-66 pubmed publisher
    ..These findings suggest that sputum [Zn] reflect clinical outcomes and underlying AI, suggesting a potential role for zinc as a biomarker in asthma. ..
  4. Zhan P, Lee E, Packman K, Tenniswood M. Induction of invasive phenotype by Casodex in hormone-sensitive prostate cancer cells. J Steroid Biochem Mol Biol. 2002;83:101-11 pubmed
    ..These observations have significant implications in the treatment of prostate cancer, since the appearance of a more aggressive phenotype following treatment is clearly undesirable. ..
  5. Fuse H, Korenaga S, Sakari M, Hiyama T, Ito T, Kimura K, et al. Non-steroidal antiandrogens act as AF-1 agonists under conditions of high androgen-receptor expression. Prostate. 2007;67:630-7 pubmed
    ..This partial antagonistic property of antiandrogens may be a molecular mechanism by which prostate cancer develops resistance to these drugs. ..
  6. Hara T, Miyazaki J, Araki H, Yamaoka M, Kanzaki N, Kusaka M, et al. Novel mutations of androgen receptor: a possible mechanism of bicalutamide withdrawal syndrome. Cancer Res. 2003;63:149-53 pubmed
    ..Our data strongly support the hypothesis that AR mutation is one possible mechanism of the AWS and suggest that flutamide might be effective as a second-line therapy for refractory PC previously treated with bicalutamide. ..
  7. Bai V, Cifuentes E, Menon M, Barrack E, Reddy G. Androgen receptor regulates Cdc6 in synchronized LNCaP cells progressing from G1 to S phase. J Cell Physiol. 2005;204:381-7 pubmed
    ..AR may play an important role in the onset of DNA synthesis in prostate cancer cells by regulating the expression and stability of Cdc6, which is critically required for the assembly of the pre-replication complex(pre-RC). ..
  8. Hobisch A, Fritzer A, Comuzzi B, Fiechtl M, Malinowska K, Steiner H, et al. The androgen receptor pathway is by-passed in prostate cancer cells generated after prolonged treatment with bicalutamide. Prostate. 2006;66:413-20 pubmed
    ..Our data may suggest that a more differentiated approach in targeting the androgen receptor is needed in prostate cancers that become resistant to classic endocrine treatment. ..
  9. Yuan X, Li T, Wang H, Zhang T, Barua M, Borgesi R, et al. Androgen receptor remains critical for cell-cycle progression in androgen-independent CWR22 prostate cancer cells. Am J Pathol. 2006;169:682-96 pubmed
    ..These results reveal a potentially critical function of AR in androgen-independent PCa that is distinct from its previously described transcriptional or nontranscriptional functions. ..
  10. Scattoni V, Montironi R, Mazzucchelli R, Freschi M, Nava L, Losa A, et al. Pathological changes of high-grade prostatic intraepithelial neoplasia and prostate cancer after monotherapy with bicalutamide 150 mg. BJU Int. 2006;98:54-8 pubmed
    ..Involution and epithelial shrinkage of prostate cancer and HGPIN were evident after neoadjuvant treatment with bicalutamide 150 mg. There was no evidence of the emergence of higher-grade cancer after treatment. ..
  11. Wang Y, Kreisberg J, Bedolla R, Mikhailova M, deVere White R, Ghosh P. A 90 kDa fragment of filamin A promotes Casodex-induced growth inhibition in Casodex-resistant androgen receptor positive C4-2 prostate cancer cells. Oncogene. 2007;26:6061-70 pubmed
    ..Our results demonstrate that expression of nuclear FlnA is necessary for androgen dependence in these cells. ..
  12. Arnold J, Liu X, Allen J, Le H, McFann K, Blackman M. Androgen receptor or estrogen receptor-beta blockade alters DHEA-, DHT-, and E(2)-induced proliferation and PSA production in human prostate cancer cells. Prostate. 2007;67:1152-62 pubmed
    ..These findings support involvement of both AR and ERbeta in mediating DHEA-, DHT-, and E(2)-induced PSA expression in prostate cancer cells. ..
  13. Festuccia C, Gravina G, Angelucci A, Millimaggi D, Muzi P, Vicentini C, et al. Additive antitumor effects of the epidermal growth factor receptor tyrosine kinase inhibitor, gefitinib (Iressa), and the nonsteroidal antiandrogen, bicalutamide (Casodex), in prostate cancer cells in vitro. Int J Cancer. 2005;115:630-40 pubmed
    ..This causes a significant delay in the onset of EGFR-driven androgen independence. ..
  14. Dupre D, Le Gouill C, Gingras D, Rola Pleszczynski M, Stankova J. Inverse agonist activity of selected ligands of the cysteinyl-leukotriene receptor 1. J Pharmacol Exp Ther. 2004;309:102-8 pubmed
    ..We demonstrate here that Montelukast, MK571, and Zafirlukast can act as inverse agonists on the human CysLT(1) receptor. ..
  15. Lee E, Zhan P, Schallhom R, Packman K, Tenniswood M. Antiandrogen-induced cell death in LNCaP human prostate cancer cells. Cell Death Differ. 2003;10:761-71 pubmed
  16. Creticos P, Knobil K, Edwards L, Rickard K, Dorinsky P. Loss of response to treatment with leukotriene receptor antagonists but not inhaled corticosteroids in patients over 50 years of age. Ann Allergy Asthma Immunol. 2002;88:401-9 pubmed
  17. Su Z, Limberis J, Martin R, Xu R, Kolbe K, Heinemann S, et al. Functional consequences of methionine oxidation of hERG potassium channels. Biochem Pharmacol. 2007;74:702-11 pubmed
    ..In contrast, the reversal potential, inactivation kinetics, and voltage-dependence of steady-state inactivation remained unaltered. Our results demonstrate that the redox status of methionine is an important modulator of hERG channel. ..
  18. Marcelli M, Stenoien D, Szafran A, Simeoni S, Agoulnik I, Weigel N, et al. Quantifying effects of ligands on androgen receptor nuclear translocation, intranuclear dynamics, and solubility. J Cell Biochem. 2006;98:770-88 pubmed
    ..These results further support the notion that ligand specific interactions rapidly affect receptor and co-factor organization, solubility, and molecular dynamics, and each can be aberrantly affected by mutation and overexpression. ..
  19. Gioeli D, Black B, Gordon V, Spencer A, Kesler C, Eblen S, et al. Stress kinase signaling regulates androgen receptor phosphorylation, transcription, and localization. Mol Endocrinol. 2006;20:503-15 pubmed
    ..Our data suggest that stress kinase signaling and nuclear export regulate AR transcriptional activity. ..
  20. Kokontis J, Hsu S, Chuu C, Dang M, Fukuchi J, Hiipakka R, et al. Role of androgen receptor in the progression of human prostate tumor cells to androgen independence and insensitivity. Prostate. 2005;65:287-98 pubmed
    ..Increased AR expression determines whether prostate cancer cells are repressed by androgen, but is not required for androgen independence. These results may have implications for anti-AR therapy for prostate cancer. ..
  21. Ghosh P, Malik S, Bedolla R, Wang Y, Mikhailova M, Prihoda T, et al. Signal transduction pathways in androgen-dependent and -independent prostate cancer cell proliferation. Endocr Relat Cancer. 2005;12:119-34 pubmed
    ..Rapamycin, an mTOR inhibitor, had a growth-inhibitory effect in C4-2 cells, but not in LNCaP cells. Our data suggest a shift from a Casodex-sensitive proliferation pathway in LNCaP cells to a rapamycin-sensitive pathway in C4-2 cells. ..
  22. Pandini G, Mineo R, Frasca F, Roberts C, Marcelli M, Vigneri R, et al. Androgens up-regulate the insulin-like growth factor-I receptor in prostate cancer cells. Cancer Res. 2005;65:1849-57 pubmed
    ..Anti-androgen therapy may be only partially effective, or almost ineffective, in blocking important biological effects of androgens, such as activation of the IGF system. ..
  23. Ellwood Yen K, Wongvipat J, Sawyers C. Transgenic mouse model for rapid pharmacodynamic evaluation of antiandrogens. Cancer Res. 2006;66:10513-6 pubmed
    ..ARR2 Pb-Lux mice provide a novel method for rapid pharmacodynamic evaluation of novel pharmacologic compounds designed to inhibit androgen receptor signaling. ..
  24. Prescott J, Jariwala U, Jia L, Cogan J, Barski A, Pregizer S, et al. Androgen receptor-mediated repression of novel target genes. Prostate. 2007;67:1371-83 pubmed
    ..Many more genes likely share AR-mediated gene repression through distal regulatory elements. Further study of such targets and their transcriptional regulation may help explain the receptor's tumorigenicity in PCa. ..
  25. Masiello D, Cheng S, Bubley G, Lu M, Balk S. Bicalutamide functions as an androgen receptor antagonist by assembly of a transcriptionally inactive receptor. J Biol Chem. 2002;277:26321-6 pubmed
    ..These results demonstrate that bicalutamide stimulates the assembly of a transcriptionally inactive AR on DNA and support altered coactivator (or corepressor) expression as a mechanism of bicalutamide-resistant androgen-independent PCa. ..
  26. Balk S. Androgen receptor as a target in androgen-independent prostate cancer. Urology. 2002;60:132-8; discussion 138-9 pubmed
    ..Understanding the mechanisms responsible for AR function in androgen-independent prostate cancer should allow the more rational development of antagonists that can enhance the efficacy of androgen ablation therapies. ..
  27. Anderson J. The role of antiandrogen monotherapy in the treatment of prostate cancer. BJU Int. 2003;91:455-61 pubmed
    ..Bicalutamide has a more favourable side-effect profile than the other antiandrogens and is more likely to promote compliance. ..
  28. Kang Z, Janne O, Palvimo J. Coregulator recruitment and histone modifications in transcriptional regulation by the androgen receptor. Mol Endocrinol. 2004;18:2633-48 pubmed
  29. Baron S, Manin M, Beaudoin C, Leotoing L, Communal Y, Veyssiere G, et al. Androgen receptor mediates non-genomic activation of phosphatidylinositol 3-OH kinase in androgen-sensitive epithelial cells. J Biol Chem. 2004;279:14579-86 pubmed
    ..Together, these novel findings point out an important and physiologically relevant link between androgens and the PI3-K/AKT signaling pathway in governing cell survival. ..
  30. Koochekpour S, Lee T, Wang R, Culig Z, Delorme N, Caffey S, et al. Prosaposin upregulates AR and PSA expression and activity in prostate cancer cells (LNCaP). Prostate. 2007;67:178-89 pubmed
    ..This finding, together with the growth-promoting effect and overexpression of prosaposin, may support a growth advantage to AI prostate cancer cells. ..
  31. See W, Wirth M, McLeod D, Iversen P, Klimberg I, Gleason D, et al. Bicalutamide as immediate therapy either alone or as adjuvant to standard care of patients with localized or locally advanced prostate cancer: first analysis of the early prostate cancer program. J Urol. 2002;168:429-35 pubmed
    ..This benefit must be balanced with the morbidity associated with long-term hormonal therapy. Followup is ongoing to determine potential survival benefits of this treatment approach. ..
  32. Michalczyk A, Allen J, Blomeley R, Ackland M. Constitutive expression of hZnT4 zinc transporter in human breast epithelial cells. Biochem J. 2002;364:105-13 pubmed
    ..We conclude that hZnT4 is constitutively expressed in the human breast and may be one of the several members of the ZnT family involved in the transport of zinc into milk. ..
  33. Lorenzo P, Saatcioglu F. Inhibition of apoptosis in prostate cancer cells by androgens is mediated through downregulation of c-Jun N-terminal kinase activation. Neoplasia. 2008;10:418-28 pubmed
    ..These data suggest that the crosstalk between AR and JNK pathways may have important implications in prostate cancer progression and may provide targets for the development of new therapies. ..
  34. Kassmann M, Hansel A, Leipold E, Birkenbeil J, Lu S, Hoshi T, et al. Oxidation of multiple methionine residues impairs rapid sodium channel inactivation. Pflugers Arch. 2008;456:1085-95 pubmed publisher
    ..This arrangement using multiple Met residues confers a finely graded oxidative modulation of Na(V) channels and allows organisms to adapt to a variety of oxidative stress conditions, such as ischemic reperfusion. ..
  35. Lin H, Lu J, Laflamme P, Qiao S, Shayegan B, Bryskin I, et al. Inter-related in vitro effects of androgens, fatty acids and oxidative stress in prostate cancer: a mechanistic model supporting prevention strategies. Int J Oncol. 2010;37:761-6 pubmed
    ..These results therefore support the rationale for PC prevention using 5-alpha reductase inhibitors, dietary restrictions or anti-oxidants, each of which has different inhibitory but complementary effects...
  36. Nawaz H, Pires P, El Seoud O. Kinetics and mechanism of imidazole-catalyzed acylation of cellulose in LiCl/N,N-dimethylacetamide. Carbohydr Polym. 2013;92:997-1005 pubmed publisher
    ..Relative to the uncatalyzed reaction, the diazole-mediated one is associated with smaller enthalpy- and larger entropy of activation, due to difference of the acylating agent. ..
  37. Jiang H, Fu W, Chen H. Palladium-catalyzed cross-coupling reactions of electron-deficient alkenes with N-tosylhydrazones: functional-group-controlled C-C bond construction. Chemistry. 2012;18:11884-8 pubmed publisher
    ..These cascade transformations present remarkable stereoselectivity and a high synthetic potential. The presence of water substantially promotes both reaction routes. ..
  38. Kosobokov M, Dilman A, Levin V, Struchkova M. Difluoro(trimethylsilyl)acetonitrile: synthesis and fluoroalkylation reactions. J Org Chem. 2012;77:5850-5 pubmed publisher
    ..The obtained silane served as a good cyanodifluoromethylating reagent toward aldehydes, N-tosylimines, N-alkylimines, and enamines under basic or acidic conditions. ..
  39. Katagiri T, Katayama Y, Taeda M, Ohshima T, Iguchi N, Uneyama K. Preparation of optically pure ?-trifluoromethyl-?-amino acids from N-tosyl-2-trifluoromethyl-2-alkyloxycarbonyl aziridine. J Org Chem. 2011;76:9305-11 pubmed publisher
  40. Meulenbeld H, de Bono J, Tagawa S, Whang Y, Li X, Heath K, et al. Tolerability, safety and pharmacokinetics of ridaforolimus in combination with bicalutamide in patients with asymptomatic, metastatic castration-resistant prostate cancer (CRPC). Cancer Chemother Pharmacol. 2013;72:909-16 pubmed publisher
  41. Bian X, Wang Q, Ke C, Zhao G, Li Y. A new series of N2-substituted-5-(p-toluenesulfonylamino)phthalimide analogues as ?-glucosidase inhibitors. Bioorg Med Chem Lett. 2013;23:2022-6 pubmed publisher
  42. Tosetti V, Sassone J, Ferri A, Taiana M, Bedini G, Nava S, et al. Transcriptional role of androgen receptor in the expression of long non-coding RNA Sox2OT in neurogenesis. PLoS ONE. 2017;12:e0180579 pubmed publisher
    ..Our findings also suggest that AR participates in embryonic neurogenesis through transcriptional control of the long non-coding RNA Sox2OT. ..
  43. Liburdi K, Straniero R, Benucci I, Vittoria Garzillo A, Esti M. Lysozyme immobilized on micro-sized magnetic particles: kinetic parameters at wine pH. Appl Biochem Biotechnol. 2012;166:1736-46 pubmed publisher
    ..In addition, LYZ-TSA seems to be the best biocatalyst for further applications in winemaking. ..
  44. Nagase H, Koyano K, Wada N, Hirayama S, Watanabe A, Nemoto T, et al. Synthesis of novel triplet drugs with 1,3,5-trioxazatriquinane skeletons and their pharmacologies. Part 2: Synthesis of novel triplet drugs with the epoxymethano structure (capped homotriplet). Bioorg Med Chem Lett. 2011;21:6198-202 pubmed publisher
    ..KNT-123 may serve as a useful tool for the study of the pharmacological actions mediated specifically via the ? receptor. ..
  45. Wang L, Du C, Lv J, Wei W, Cui Y, Xie X. Antiasthmatic drugs targeting the cysteinyl leukotriene receptor 1 alleviate central nervous system inflammatory cell infiltration and pathogenesis of experimental autoimmune encephalomyelitis. J Immunol. 2011;187:2336-45 pubmed publisher
    ..These effects can be blocked by CysLT1 antagonists. Our findings indicate that the antiasthmatic drugs against CysLT1 can also be used to treat multiple sclerosis. ..
  46. Suehiro M, Yang G, Torchon G, Ackerstaff E, Humm J, Koutcher J, et al. Radiosynthesis of the tumor hypoxia marker [18F]TFMISO via O-[18F]trifluoroethylation reveals a striking difference between trifluoroethyl tosylate and iodide in regiochemical reactivity toward oxygen nucleophiles. Bioorg Med Chem. 2011;19:2287-97 pubmed publisher
    ..Thus, this investigation has identified 2,2,2-[(18)F]trifluoroethyl tosylate as an excellent [(18)F]trifluoroethylating agent, which can convert efficiently an alcohol into the corresponding [(18)F]trifluoroethyl ether. ..
  47. Kawata H, Arai S, Nakagawa T, Ishikura N, Nishimoto A, Yoshino H, et al. Biological properties of androgen receptor pure antagonist for treatment of castration-resistant prostate cancer: optimization from lead compound to CH5137291. Prostate. 2011;71:1344-56 pubmed publisher
    ..Agonist metabolite diminished the antitumor activity of AR pure antagonist. CH5137291 exhibited antitumor activity in LNCaP-BC2 and VCaP-CRPC xenograft models, suggesting that the compound has potential for the treatment of CRPC. ..
  48. Tang S, Takeda M, Nakao Y, Hiyama T. Nickel-catalysed cross-coupling reaction of aryl(trialkyl)silanes with aryl chlorides and tosylates. Chem Commun (Camb). 2011;47:307-9 pubmed publisher
  49. Bardhan M, Bhattacharya S, Misra T, Mukhopadhyay R, De A, Chowdhury J, et al. Nonradiative inter- and intramolecular energy transfer from the aromatic donor anisole to a synthesized photoswitchable acceptor system. Spectrochim Acta A Mol Biomol Spectrosc. 2010;75:647-55 pubmed publisher
  50. Jaffer S, Oesterle L, Newman S. Storage media effect on bond strength of orthodontic brackets. Am J Orthod Dentofacial Orthop. 2009;136:83-6 pubmed publisher
    ..Dry, formalin, and ethanol storage should be avoided. Water, isotonic saline solution, and chloramine T storage produced comparable bond strengths. Rinsing or not rinsing had no effect on bond strength with these storage media. ..
  51. Chun J, Pike V. Regiospecific syntheses of functionalized diaryliodonium tosylates via [hydroxy(tosyloxy)iodo]arenes generated in situ from (diacetoxyiodo)arenes. J Org Chem. 2012;77:1931-8 pubmed publisher
    ..The described methodology broadens the scope for producing new functionalized diaryliodonium salts for diverse applications. ..
  52. Chowdhury C, Das B, Mukherjee S, Achari B. Palladium-catalyzed approach for the general synthesis of (E)-2-arylmethylidene-N-tosylindolines and (E)-2-arylmethylidene-N-tosyl/nosyltetrahydroquinolines: access to 2-substituted indoles and quinolines. J Org Chem. 2012;77:5108-19 pubmed publisher
    ..The reactions proceeded efficiently with a wide variety of substrates and afforded the corresponding products in moderate to excellent yields. ..
  53. Goverdhan G, Reddy A, Srinivas K, Himabindu V, Reddy G. Identification, characterization and synthesis of impurities of zafirlukast. J Pharm Biomed Anal. 2009;49:895-900 pubmed publisher
    ..The separation of the impurities by reverse phase HPLC, the confirmation of their structures by IR, MS and NMR spectral data, the mechanism of their formation and their syntheses are discussed in detail. ..