1,2,5-Substituted derivatives of 2-phenylpyrrolidine

Tamazyan, R. А.; Karapetyan, H.A.; Martirisyan, Ashot; Martirosyan, V. O.; Harutyunyan, G.; Gasparyan, S. P.

doi:10.1107/s0108270104007930

Cited by 3 publications

(3 citation statements)

References 2 publications

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“…3d). Except for Boc-α-phenylproline, which also crystallized in a cis conformer (Tamazyan et al 2004), α-phenyl-D-proline (Tamazyan et al 2002(Tamazyan et al , 2008 and α-(4-chlorophenyl)-D-proline (Polindara-García and Miranda 2012) appear in the γ'-basin (Fig. 2d) with an endo ring pucker.…”

Section: α-Substituted Prolinementioning

confidence: 99%

Conformational landscape of substituted prolines

Ganguly

Basu

2020

Biophys Rev

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The cyclic side chain of the amino acid proline confers unique conformational restraints on its backbone and side chain dihedral angles. This affects two equilibria-one at the backbone (cis/trans) and the other at the side chain (endo/exo). Substitutions on the proline ring impose additional steric and stereoelectronic effects that can further modulate both these equilibria, which in turn can also affect the backbone dihedral angle (ϕ, ψ) preferences. In this review, we have explored the conformational landscape of several termini capped mono-(2-, 3-, 4-, and 5-) substituted proline derivatives in the Cambridge Structural Database, correlating observed conformations with the nature of substituents and deciphering the underlying interactions for the observed structural biases. The impact of incorporating these derivatives within model peptides and proteins are also discussed for selected cases. Several of these substituents have been used to introduce bioorthogonal functionality and modulate structure-specific ligand recognition or used as spectroscopic probes. The incorporation of these diversely applicable functional groups, coupled with their ability to define an amino acid conformation via stereoelectronic effects, have a broad appeal among chemical biologists, molecular biophysicists, and medicinal chemists.

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Section: α-Substituted Prolinementioning

confidence: 99%

Conformational landscape of substituted prolines

Ganguly

Basu

2020

Biophys Rev

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“…For general background, see: Taylor et al (1998); Jeng et al (2002); Anderson et al (2004); Ryder et al (2000). For biological activity of the title compound, see: Tamazyan et al (2004). For graph-set notation of hydrogen bonding, see: Bernstein et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

“…Also, due to their structural diversity and functional versatility, they are widely used as chiral building blocks and molecular scaffolds in pharmaceutics (Taylor et al, 1998;Ryder et al, 2000;Jeng et al, 2002). N-Butoxycarbonyl-(S)-αbenzyl proline, a closely related analogue of the title compound N-tert-butoxycarbonyl-α-(2-fluorobenzyl)-L-proline, is a potential non-nucleoside reverse transcriptase inhibitor in anti-human-immunodeficiency virus type-1 (Tamazyan et al, 2004).…”

Section: Data Collectionmentioning

confidence: 99%

N-tert-Butoxycarbonyl-α-(2-fluorobenzyl)-L-proline

Rajalakshmi¹,

Srinivasan²,

Krishnakumar³

et al. 2013

Acta Cryst E

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In the title compound, C17H22FNO4, the pyrrolidine ring adopts an envelope conformation with the disordered components of the methylene C atom, with site occupancies of 0.896 (7) and 0.104 (7), being the flap on either side of the mean plane involving the other atoms of the ring. The carboxylic acid group forms dihedral angles of 72.06 (11) and 45.44 (5)° with the N-tert-butoxycarbonyl group and the 2-fluorobenzyl group, respectively. In the crystal, two-dimensional layers of molecules parallel to (001) are built through an R 4 4(23) motif generated via O—H⋯O, C—H⋯O and C—H⋯F interactions, and an R 2 2(11) motif generated by C—H⋯O and C—H⋯F interactions.

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Crystallographic and DFT Studies on Pyrrolo[1,2-c]imidazole Scaffolds

Jayaraman

Balakrishnan

Muthu

et al. 2014

Journal of Crystallography

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The crystal structures of the compounds C15H14N4O2 (1) and C16H16N4O4 (2) are reported and analyzed by single crystal X-ray diffraction technique. Compounds (1) and (2) crystallized in monoclinic space group P21/c and Cc with four molecules in the unit cell, respectively. The unit cell parameters for compound (1) are a = 11.4501(15) Å, b = 9.7869(11) Å, c = 12.3653(15) Å, β = 90.997(11)°, and Volume = 1385.5(3) Å3 and for compound (2) are a = 13.865(2) Å, b = 6.9538(8) Å, c = 16.841(2) Å, β = 98.602(11)°, and Volume = 1605.4(4) Å3. In both compounds (1) and (2), the pyrrolidine ring adopts half-chair conformation. Moreover, both inter- and intramolecular N–H⋯O hydrogen bonds stabilize the crystal structure and play a crucial role in crystal packing. This intermolecular interaction alone constructs C11 chain motif in both compounds. It is also supported by weak intermolecular π-π interaction which is essential for the stability of the crystal packing. Further, the Density Functional Theory (B3LYP) method with standard 6-31G basis set was used in the calculation and calculated geometrical parameter is correlated with the corresponding experimental data. The obtained HOMO and LUMO energies are in negative values indicating that the compounds are in stable state.

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1,2,5-Substituted derivatives of 2-phenylpyrrolidine

Cited by 3 publications

References 2 publications

Conformational landscape of substituted prolines

Conformational landscape of substituted prolines

N-tert-Butoxycarbonyl-α-(2-fluorobenzyl)-L-proline

Crystallographic and DFT Studies on Pyrrolo[1,2-c]imidazole Scaffolds

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