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Volumn 76, Issue 5, 2011, Pages 491-496

Novel and efficient synthesis of 22-alkynyl-13,24(23)-cyclo-18,21- dinorchol-22-en-20(23)-one analogues

Author keywords

Cuprous iodide; Cyclo 18,21 dinorcholenones; Iodine; Palladium(0) catalyst; Sonogashira reaction

Indexed keywords

(3ALPHA,5ALPHA) 3 HYDROXY 22 [3 (3 HYDROXY 3 METHYLBUT 1 YNYL)] 13,23 CYCLO 18,21 DINORCHOL 22 EN 23 ONE; (3ALPHA,5ALPHA) 3 HYDROXY 22 [3 (3 HYDROXYBUT 1 YNYL)] 13,23 CYCLO 18,21 DINORCHOL 22 EN 23 ONE; (3ALPHA,5ALPHA) 3 HYDROXY 22 [3 (3 HYDROXYPROP 1 YNYL)] 13,23 CYCLO 18,21 DINORCHOL 22 EN 23 ONE; (3ALPHA,5ALPHA) 3 HYDROXY 22 [3 (4 METHYLPENT 1 YNYL)] 13,23 CYCLO 18,21 DINORCHOL 22 EN 23 ONE; (3ALPHA,5ALPHA) 3 HYDROXY 22 [3 [2 (1 HYDROXYCYCLOHEXYL)ETHYNYL]] 13,23 CYCLO 18,21 DINORCHOL 22 EN 23 ONE; (3ALPHA,5ALPHA) 3 HYDROXY 22 IODO 13,23 CYCLO 18,21 DINORCHOL 22 EN 20 ONE; (3ALPHA,5BETA) 3 HYDROXY 22 [3 (3 HYDROXYBUT 1 YNYL)] 13,24 CYCLO 18,21 DINORCHOL 22 EN 20 ONE; (3ALPHA,5BETA) 3 HYDROXY 22 [3 [2 (1 HYDROXYCYCLOHEXYL)ETHYNYL]] 13,24 CYCLO 18,21 DINORCHOL 22 EN 20 ONE; (3ALPHA,5BETA) 3 HYDROXY 22 IODO 13,24 CYCLO 18,21 DINORCHOL 22 EN 20 ONE; (3BETA,5ALPHA) 3 HYDROXY 22 [3 (3 HYDROXY 3 METHYLBUT 1 YNYL)] 13,24 CYCLO 18,21 DINORCHOL 22 EN 20 ONE; (3BETA,5ALPHA) 3 HYDROXY 22 IODO 13,24 CYCLO 18,21 DINORCHOL 22 EN 20 ONE; 22 IODOCYCLO 18,21 DINORCHOLENONE DERIVATIVE; ALKYNE; CUPROUS IODIDE; CUPROUS ION; DOXORUBICIN; PALLADIUM; STEROID; TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM; UNCLASSIFIED DRUG;

EID: 79952574757     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2011.01.005     Document Type: Article
Times cited : (11)

References (19)
  • 1
    • 77950516201 scopus 로고    scopus 로고
    • Preparation of GABA modulatory and anesthetic 24-cyclo-18,21- dinorcholanes and structurally related pentacyclic steroids
    • US Patent
    • Covey DF, Jiang X. Preparation of GABA modulatory and anesthetic 24-cyclo-18,21-dinorcholanes and structurally related pentacyclic steroids. US Patent; 2004. 59 pp.
    • (2004) , pp. 59
    • Covey, D.F.1    Jiang, X.2
  • 2
    • 0344118747 scopus 로고    scopus 로고
    • Neurosteroid analogues. 9. Conformationally constrained pregnanes: Structure-activity studies of 13,24-cyclo-18,21-dinorcholane analogues of the GABA modulatory and anesthetic steroids (3α,5β)- and (3α,5β)-3-hydroxypregnan-20-one
    • Jiang X, Manion BD, Benz A, Rath NP, Evers AS, Zorumski CF, et al. Neurosteroid analogues. 9. Conformationally constrained pregnanes: structure-activity studies of 13,24-cyclo-18,21-dinorcholane analogues of the GABA modulatory and anesthetic steroids (3α,5β)- and (3α,5β)-3-hydroxypregnan-20-one. J Med Chem 2003;46:5334-48.
    • (2003) J Med Chem , vol.46 , pp. 5334-5348
    • Jiang, X.1    Manion, B.D.2    Benz, A.3    Rath, N.P.4    Evers, A.S.5    Zorumski, C.F.6
  • 3
    • 44249099639 scopus 로고    scopus 로고
    • Synthesis of pentacyclic steroids
    • Ibrahim-Ouali M. Synthesis of pentacyclic steroids. Steroids 2008;73:775-97.
    • (2008) Steroids , vol.73 , pp. 775-797
    • Ibrahim-Ouali, M.1
  • 4
    • 40649116879 scopus 로고    scopus 로고
    • Microwave promoted one-pot synthesis of novel A-ring fused steroidal dehydropiperazines
    • Borthakur M, Barthakur MG, Boruah RC. Microwave promoted one-pot synthesis of novel A-ring fused steroidal dehydropiperazines. Steroids 2008;73:539-42.
    • (2008) Steroids , vol.73 , pp. 539-542
    • Borthakur, M.1    Barthakur, M.G.2    Boruah, R.C.3
  • 5
    • 0025218831 scopus 로고
    • Studies of novel pentacyciic heterocyclic steroids: Part XXI. Total synthesis of racemic benz[3,4]-6-oxaestra-1,3,5(10),8-tetraen-17β-ol
    • (a) Ramesh Babu B, Ramana DV, Ramadas SR. Studies of novel pentacyciic heterocyclic steroids: part XXI. Total synthesis of racemic benz[3,4]-6- oxaestra-1,3,5(10),8-tetraen-17β-ol. Steroids 1990;55:101-4;
    • (1990) Steroids , vol.55 , pp. 101-104
    • Ramesh Babu, B.1    Ramana, D.V.2    Ramadas, S.R.3
  • 6
    • 27644585901 scopus 로고    scopus 로고
    • Benzothieno and benzofurano annelated estranges
    • (b) Watanabe M, Mataka S, Thiemann T. Benzothieno and benzofurano annelated estranges. Steroids 2005;70:856-66;
    • (2005) Steroids , vol.70 , pp. 856-866
    • Watanabe, M.1    Mataka, S.2    Thiemann, T.3
  • 8
    • 44249083934 scopus 로고    scopus 로고
    • 3- and 19-Oximes of 16α,17α-cyclohexanoprogesterone derivatives: Synthesis and interactions with progesterone receptor and other proteins
    • Levina IS, Pokrovskaya EV, Kulikova LE, KamernitzkyAV, Kachala VV, Smirnov AN. 3- and 19-Oximes of 16α,17α-cyclohexanoprogesterone derivatives: synthesis and interactions with progesterone receptor and other proteins. Steroids 2008;73:815-27.
    • (2008) Steroids , vol.73 , pp. 815-827
    • Levina, I.S.1    Pokrovskaya, E.V.2    Kulikova, L.E.3    Kamernitzky, A.V.4    Kachala, V.V.5    Smirnov, A.N.6
  • 9
    • 1842503712 scopus 로고    scopus 로고
    • Anti-inflammatory effects of butadiene Diels-Alder adducts to some 1-dehydroglucocorticoids in rats
    • DOI 10.1016/j.ejps.2003.12.008, PII S0928098704000028
    • Sharifzadeh M, Ramazani F, Shamsa F. Anti-inflammatory effects of butadiene Diels-Alder adducts to some 1-dehydroglucocorticoids in rats. Eur J Pharm Sci 2004;21:575-9. (Pubitemid 38447138)
    • (2004) European Journal of Pharmaceutical Sciences , vol.21 , Issue.5 , pp. 575-579
    • Sharifzadeh, M.1    Ramazani, F.2    Shamsa, F.3
  • 12
    • 34249283732 scopus 로고    scopus 로고
    • Ene-yne tetrahydrofurans from the Sponge Xestospongia muta. Exploiting a weak CD effect for assignment of configuration
    • Morinaka BI, Skepper CK, Molinski TF. Ene-yne tetrahydrofurans from the Sponge Xestospongia muta. Exploiting a weak CD effect for assignment of configuration. Org Lett 2007;9:1975-8.
    • (2007) Org Lett , vol.9 , pp. 1975-1978
    • Morinaka, B.I.1    Skepper, C.K.2    Molinski, T.F.3
  • 13
    • 11044220599 scopus 로고    scopus 로고
    • Synthesis of 1,3-enynes via Suzuki-type reaction of vinylic tellurides and potassium alkynyltrifluoroborate salts
    • DOI 10.1016/j.tetlet.2004.11.160, PII S0040403904026711
    • Stefani HA, Cella R, Dorr FA, Pereira CMP, Zeni G, Gomes M. Synthesis of 1,3-enynes via Suzuki-type reaction of vinylic tellurides and potassium alkynyltrifluoroborate salts. Tetrahedron Lett 2005;46:563-7. (Pubitemid 40044713)
    • (2005) Tetrahedron Letters , vol.46 , Issue.4 , pp. 563-567
    • Stefani, H.A.1    Cella, R.2    Dorr, F.A.3    Pereira, C.M.P.4    Zeni, G.5    Gomes Jr., M.6
  • 14
    • 77955921669 scopus 로고    scopus 로고
    • 4/AgOAc-catalyzed coupling of 17-steroidal triflates and alkynes: Highly efficient synthesis of D-ring unsaturated 17-alkynylsteroids
    • 4/AgOAc-catalyzed coupling of 17-steroidal triflates and alkynes: highly efficient synthesis of D-ring unsaturated 17-alkynylsteroids. Steroids 2010;75:936-43.
    • (2010) Steroids , vol.75 , pp. 936-943
    • Sun, Q.1    Jiang, C.2    Xu, H.3    Zhang, Z.4    Liu, L.5    Wang, C.6
  • 15
    • 58249106934 scopus 로고    scopus 로고
    • A cooperative copper- and palladium-catalyzed three-component coupling of benzynes, allylic epoxides, and terminal alkynes
    • Jeganmohan M, Bhuvaneswari S, Cheng CH. A cooperative copper- and palladium-catalyzed three-component coupling of benzynes, allylic epoxides, and terminal alkynes. Angew Chem, Int Ed 2009;48:391-4.
    • (2009) Angew Chem, Int Ed , vol.48 , pp. 391-394
    • Jeganmohan, M.1    Bhuvaneswari, S.2    Cheng, C.H.3
  • 16
    • 33644773385 scopus 로고    scopus 로고
    • Palladium-catalyzed cross-coupling reactions of (2-pyridyl) allyldimethylsilanes with aryl iodides
    • DOI 10.1021/ol052961u
    • Nokami T, Tomida Y, Kamei T, Itami K, Yoshida J. Palladium-catalyzed cross-coupling reactions of (2-pyridyl)allyldimethylsilanes with aryl iodides. Org Lett 2006;8(4):729-31. (Pubitemid 43342001)
    • (2006) Organic Letters , vol.8 , Issue.4 , pp. 729-731
    • Nokami, T.1    Tomida, Y.2    Kamei, T.3    Itami, K.4    Yoshida, J.-I.5
  • 17
    • 67549112089 scopus 로고    scopus 로고
    • Palladium-catalyzed three-component 1:2:1 coupling of aryl iodides, alkynes, and alkenes to produce 1,3,5-hexatriene derivatives
    • Horiguchi H, Hirano K, Satoh T, Miuraa M. Palladium-catalyzed three-component 1:2:1 coupling of aryl iodides, alkynes, and alkenes to produce 1,3,5-hexatriene derivatives. Adv Synth Catal 2009;351:1431-6.
    • (2009) Adv Synth Catal , vol.351 , pp. 1431-1436
    • Horiguchi, H.1    Hirano, K.2    Satoh, T.3    Miuraa, M.4
  • 19
    • 77955920545 scopus 로고    scopus 로고
    • Stereoselective synthesis of some methyl-substituted steroid hormones and their in vitro cytotoxic activity against human gastric cancer cell line MGC-803
    • Li C, Qiu W, Yang Z, Luo J, Yang F, Liu M, et al. Stereoselective synthesis of some methyl-substituted steroid hormones and their in vitro cytotoxic activity against human gastric cancer cell line MGC-803. Steroids 2010;75:859-69.
    • (2010) Steroids , vol.75 , pp. 859-869
    • Li, C.1    Qiu, W.2    Yang, Z.3    Luo, J.4    Yang, F.5    Liu, M.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.