Polymorphism and phase transition behavior of 6,6′-bis(chloromethyl)-1,1′,4,4′-tetramethyl-3,3′-(p-phenylenedimethylene)bis(piperazine-2,5-dione)

Abstract

A crystallographic investigation of the title compound, C22H28Cl2N4O4, using crystals obtained under different crystallization conditions, revealed the presence of two distinct polymorphic forms. The molecular conformation in the two polymorphs is very different: one adopts a `C' shape, whereas the other adopts an `S' shape. In the latter, the molecule lies across a crystallographic twofold axis. The `S'‐shaped polymorph undergoes a reversible orthorhombic‐to‐monoclinic phase transition on cooling, whereas the structure of the `C'‐shaped polymorph is temperature insensitive.

Conformational Polymorphism

“…The molecule with CSD refcode QUBPAF crystallizes with a stable folded conformer (C-shaped) in which the two ends of the molecule interact through favorable intramolecular interactions (dispersion and electrostatics) and a metastable unfolded conformer (S-shaped) in which the increased distance precludes such interactions. 86 Finally, bicalutamide, a pharmaceutically active compound, crystallizes with a pair of conformers showing the largest ΔE gas−gas value of 37 kJ/mol (JAYCES). 87 The stable gas-phase conformer crystallizes in the metastable polymorph and consists of a self-folded geometry (JAYCES02) with an intramolecular hydrogen bond (between the OH and SO 2 groups).…”

3D-MOLECULAR SCREENING OF DIKETOPIPERAZINE DERIVATES ON Staphylococcus aureus DEHYDROSQUALENE SYNTHASE USING VINA

“…Its activity is influenced by functional group of phenolic in curcumin (Naz et al, 2010;Sunilson et al, 2009;Rai et al, 2008;Cikrikci et al, 2008). Previous research have proven that diketopiperazine derivatives have antimicrobial activity (Santoso et al, 2011;Villemin and Alloum, 1990), oxytocin antagonist (Borthwick et al, 2009), cell growth inhibition, cytostatic, and cytotoxic (Andreani et al, 2008), anticancer of sporidesmins analogues (Polaske et al, 2009), antioxidant (Santoso and Supardjan, 2010), and antileishmanial in vitro in Leishmania donovani (Hazra et al, 2007). Santoso (2010) has done a molecular docking of diketopiperazine derivates on tubulin, the limiting factor in the cycle process of breast cancer in cell line T47D (Da'i et al, 2007).…”

Docking Analog Kurkumin Turunan Piperazindion Dengan Tubulin (1tub) Rantai  Menggunakan Vina Dan Autodock1

“…Piperazindion dapat digunakan sebagai pengganti gugus tengah diketon kurkumin dan dengan mempertahankan gugus samping PGV-0 dan PGV-1 diperoleh senyawa turunan piperazindion. Beberapa turunan piperazindion telah diteliti dan memiliki aktivitas inhibisi pertumbuhan sel, sitostatik, dan sitotoksik (Andreani et al, 2008), dan antikanker sporidesmins merupakan turunan piperazin-2,5-dion (Polaske et al, 2009). Pembuktian adanya aktivitas ini dapat dilakukan melalui teknik molecular docking terhadap salah satu protein yang ditenggarai paling banyak berperan dalam siklus sel kanker, yaitu tubulin (Davis et al, 1999…”