Paper Titles in Periodical
International Letters of Chemistry, Physics and Astronomy
ILCPA Volume 33

Subscribe to our Newsletter and get informed about new publication regulary and special discounts for subscribers!

ILCPA > ILCPA Volume 33 > Conformational Analysis, Substituent Effect and...
< Back to Volume

Conformational Analysis, Substituent Effect and Structure Activity Relationships of 16-Membered Macrodiolides

Full Text PDF


Electronic structures, Conformational Analysis, effect of the substitution and structure activity Relationships for macrodiolides, have been studied by PM3 and ab initio methods. In the present work, the calculated values, namely net charges, bond lengths, MESP, dipole moments, electron-affinities, heats of formation, drug-likeness and QSAR properties, are reported and discussed in terms of the biological activity of macrodiolides.


International Letters of Chemistry, Physics and Astronomy (Volume 33)
R. Mazri et al., "Conformational Analysis, Substituent Effect and Structure Activity Relationships of 16-Membered Macrodiolides", International Letters of Chemistry, Physics and Astronomy, Vol. 33, pp. 146-167, 2014
Online since:
May 2014

E.M. Driggers, S.P. Hale, J. Lee, N.K. Terrett, Nat. Rev. Drug Discov. 7(2008) 608-624.

J. Mallinson, I. Collins, Fut. Med. Chem. 4 (2012) 1409-1438.

E. J. Kang, E. Lee, Chem. Rev. 105 (2005) 4348-4378.

S. Muthusamy, M. Sivaguru, Tetrahedron. Lett 54 (2013) 6810-6813.

(a) P. Magiatis, D. Spanakis, S. Mitaku, E. Tsitsa, A. Mentis, C.J. Harvala, Nat. Prod. 64 (2001).

(a) E. M. Driggers, S. P. Hale, J. Lee, N. K. Terrett, Nat. Rev. Drug Disc. 7 (2007) 608624; (b) E. Marsault, M. L. Peterson, J. Med. Chem. 54 (2011) 1961-(2004).

D. F. Veber, S. R. Johnson, H. -Y. Cheng, B. R. Smith, K. W. Ward, K. D. Kopple, J. Med. Chem. 45 (2002) 2615-2623.

S. Omura, Macrolide Antibiotics: Chemistry, Biology and Practice; Academic: New York, 1984, 538.

J. S. Yadav, U. V. Subba Reddy, B. V. Subba Reddy, Tetrahedron. Letters 50 (2009) 5984-5986.

J. G. Topliss, Perspect. Drug. Discov. Des. 1 (1993) 253.

W. Zhigao, W. Fangqiang, Su. Changhua, Z. Yongling, J. Comput. Theor. Nanosci. 10 (2013) 2323-2327.

A. Eghdami, M. Monajjemi, Quantum Matter 2 (2013) 324-331.

Y. Chen, Di. Xu, M. Yang, J. Comput. Theor. Nanosci. 10 (2013) 2916-2919.

B. Wu, X. Kong, Z. Cao, Y. Pan, Y. Ren, Y. Li, Q. Yang, and F. Lv, J. Comput. Theor. Nanosci. 10(2013) 2403-2410.

M. Ciobanu, L. Preda, D. Savastru, R. Savastru, E. M. Carstea, Quantum. Matter. 2 (2013) 60.

S. Anurag, J. Srashti, A. K. Nagawat, Quantum. Matter. 2 2013) 469-473.

A. Srivastava, N. Saraf, A. K. Nagawat, Quantum. Matter. 2 (2013) 401-407.

A. Srivastava, N. Jain, A. K. Nagawat, Quantum. Matter. 2 (2013) 307-313.

M. Joydeep, Ch. Raja, S. Saikat, V. Anjay, De. Biplab, T. K. Ravi, Der. Pharma. Chemica 1(2) (2009) 188-198.

HyperChem (Molecular Modeling System) Hypercube, Inc. USA, (2007).

J. J. P. Stewart, J. Comput. Chem. 10 (1989) 221-264.

S. Belaidi, M. Laabassi, R. Gree, A. Botrel. Scientific Study & Research 4 (2003) 27-38.

S. Belaidi, N. Melkemi, Asian Journal of Chemistry 25 (2013) 4527-4531.

I. Fleming, Frontier Orbitals and Organic Chemical Reactions (John Wiley and Sons, NewYork, 1976, 5-27.

J. S. Murray, K. Sen, Molecular Electrostatic Potentials, Concepts and Applications Elsevier, Amsterdam, (1996).

I. Alkorta, J. J. Perez, Int. J. Quant. Chem. 57 (1996) 123.

E. Scrocco, J. Tomasi, Adv. Quantum Chem. 11 (1978) 115.

J. Sponer, P. Hobza, Int. J. Quant. Chem. 57 (1996) 959.

F. J. Luque, M. Orozco, P. K. Bhadane, S. R. Gadre, J. Phys. Chem. 97 (1993) 9380.

G. L. Miessler., D. A. Tarr. Inorganic. Chemistry, 2nd ed, Prentice-Hall Upper Saddle River, NJ, USA. (1999).

R. P. Verma, A. Kurup, C. Hansch, Bioorganic & Medicinal Chemistry 13 (2005) 237255.

W. J. Lyman, Rosenblatt, Eds.; American Chemical Society: Washington. DC., 1-1-151, (1990).

A. Sabljic, H. Guesten, J. Hermens, A. Opperhuizen, Environmental Science & Technology 27 (1993) 1394-1402.

C. Hansch, A. J. Leo, Wiley: New York, (1979).

T. Suzuki, Y. Kudo, Journal of Computer-Aided Molecular Design 4 (1990) 155-198.

A. Khalafi-Nezhad, M. N. Soltani Rad, H. Mohabatkar, Z. Asrari, B. Hemmateenejad, Bioorg. Med. Chem. 13 (2005) 1931-(1938).

H. Liu, Y. -M. Du, J. F. Kennedy, Carbohydrate. Polymers. 68 (2007) 598-600.

G. E. Chudinov, D. V. Napolov, M. V. Basilevsky, Chemical. Physics 160 (1992) 4154.

P. D. Leeson, A. M. Davis, J. Med. Chem. 47 (2004) 6338-6348.

M. Yadav, Bioinformation 7 (2011) 388-392.

L. K. Ojha, Ajay M. Chaturvedi, A. Bhardwaj, M. Thakur,A. Thakur, IJPAC 3(4) (2013) 417-427.

M. Yadav, Bioinformation ., 7(8) (2011) 388-392.

S. Winiwarter, N. M. Bonham, F. Ax, A. Hallberg, H. Lennerna¨s, A. Karlen, J. Med. Chem. 41 (1998) 4939-4949.

P. Artursson, J. Karlsson, Biochem. Biophys. Res. Commun. 175 (1991) 880-885.

R. C. Young, R. C. Mitchell, Th. H. Brown, C. R. Ganellin, R. Griffiths, M. Jones, K. K. Rana, D. Saunders, I. R. Smith, N. E. Sore, T. J. Wilks, J. Med. Chem. 31 (1988) 656671.

H. Van de Waterbeemd, G. Camenisch, G. Folkers, J. R. Chre´tien, O. A. Raevsky, J. Drug. Target. 2 (1998) 151-165.

D. A. Smith, B. C. Jones, D. K. Walker, Med. Res. Rev. 16 (1996) 243-266.

H. Pajouhesh, G. R. Lenz, Neurotherapeutics 2 (2005) 541.

R. Panchagnula , N. S. Thomas, Int. J. Pharm. 201 (2000) 131-150.

P. Lalitha, S. Sivakamasundari, Orient. J. Chem. 26(1) (2010) 135-141.

J. Wang, X.Q. Xie, T. Hou, X. Xu, Fast J. Phys. Chem. A. 24; 111(20) (2007) 44434448.

S. Lanners, H. Norouzi-Arasi, Xavier J. Salom-Roig, G. Hanquet , A. Chemie 119 (2007) 7216-7219.

A. Gavezzotti, J. Am. Chem. Soc. 105 (1983) 5220-5225.

O. Germay, N. Kumar, Eric. J. Thomas, Tetrahedron. Lett, 42, 30, 23 (2001) 49694974.

H. R. Jois, A. Sarkar, S. Gurusiddaiah, Antimicrob. Agents Chemother 30(3) (1986) 458.

T. K. Chakraborty, V. R. Reddy, A. Kumar, Tetrahedron. Lett, 47, 42 (2006) 74357438.

O. Kattnig, E. Furstner, J. Am. Chem. Soc. 126 (2004) 15970-15971.

S. Amigoni, Y. Le Floc'h, Tetrahedron: Asymmetry, 8, 16 (1997) 2827-2831.

J. Gailliard, Synthese formelle de la pyrenophorine, Thèse de doctorat en Chimie; université de Rouen. (1990).

A. Noda, S. Aoyagi, N. Machinaga, Ch. Kibayashi, Tetrahedron. Lett. 35, 44 (1994) 8237-8240.

I. Paterson, J. Man. Tetrahedron. Lett, 38, 4 (1997) 695-698.

R. Barth, J. Mulzer , Tetrahedron. 64, 21 (2008) 4718-4735.

S. Belaidi, M. Omari , J. Soc. Alger. Chim. 10 (2000) 31-40.

S. Belaidi, M. Omari et A. Dibi, J. Soc. Alger. Chim. 10(2) (2000) 221.

S. Belaidi, A. Dibi, M. Omari, Turk. J. Chem. 26 (2002) 491-500.

S. Belaidi, M. Omari, T. Lanez, A. Dibi, J. Soc. Alger. Chim. 14 (2004) 27-39.

S. Belaidi., T. Lanez, M. Omari, A. Botrel. Asian J. Chem. 17 (2005) 859-870.

S. Belaidi, M. Laabassi, R. Gree, A. Botrel, Rev. Roum. Chim. 50 (2005) 759-765.

S. Belaidi, D. Harkati, ISRN Organic Chemistry, (2011) 594242.

E. H. Kerns, L. Di, Academic. Press, USA. (2008) 43-47.

V. Pliska, B. Testa, H. van de Waterbeemd, R. Mannhold, H. Kubinyi, H. Timmerman, Lipophilicity in Drug Action and Toxicology, Wiley-VCH, Federal Republic of Germany (1996).

B. Yavorski, A. Detlaf, Checklist of Physics. 1980, 376.

TAMMO Theoretical Analysis of Molecular Membrane Organization, CRC Press, Boca Raton, Florida, USA (1995).

Deleu M Synthesis of Surfactin Derivatives and Study Their Properties, Thesis Ph. D, FUSAGX, Belgique (2000).

L. B. Kier, Molecular Orbital Theory in Drug Research, Academic Press. New York. NY. USA (1981).

E. H. Kerns, L. Di, Drug-like Properties: Concepts, Structure Design and Methods: from ADME to Toxicity Optimization, Academic Press, USA, (2008) 43-47.

Ch. A. Lipinski, Franco Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Deliv. Rev. 64 (2012) 4-17.

G. Vistoli, A. Pedretti, B. Testa, Drug. Discov. Today. 13(7-8) (2008) 285-294.

C. A. Lipinski, F. Lombardo, B. Dominy, W. P. J. Feeney. Adv. Drug. Deliv. Rev. 23 (1997) 3-25. ( Received 01 May 2014; accepted 08 May 2014 ).

Show More Hide
Cited By:

[1] T. Salah, S. Belaidi, N. Melkemi, I. Daoud, S. Boughdiri, "In silico investigation by conceptual DFT and molecular docking of antitrypanosomal compounds for understanding cruzain inhibition", Journal of Theoretical and Computational Chemistry, Vol. 15, p. 1650021, 2016


[2] M. Salvatore, M. DellaGreca, R. Nicoletti, F. Salvatore, F. Vinale, D. Naviglio, A. Andolfi, "Talarodiolide, a New 12-Membered Macrodiolide, and GC/MS Investigation of Culture Filtrate and Mycelial Extracts of Talaromyces pinophilus", Molecules, Vol. 23, p. 950, 2018