57644-24-3Relevant articles and documents
Rationalizing Distinct Mechanical Properties of Three Polymorphs of a Drug Adduct by Nanoindentation and Energy Frameworks Analysis: Role of Slip Layer Topology and Weak Interactions
Raju, K. Bal,Ranjan, Subham,Vishnu,Bhattacharya, Manjima,Bhattacharya, Biswajit,Mukhopadhyay, Anoop K.,Reddy, C. Malla
, p. 3927 - 3937 (2018)
Three concomitant polymorphs of 3-((4-chlorophenyl)imino)indolin-2-one, a Schiff's base, are identified and sorted based on morphology and mechanical response of their crystals. Form I grows as blocks and shows brittle fracture, Form II has long needles and shows plastic bending, and Form III also has long needles and shows elastic bending under similar qualitative mechanical deformation tests. Furthermore, the brittle Form I was found to exhibit thermosalient behavior (jumping) when heated on a hot plate. The distinct mechanical behavior of the three forms is rationalized by analyzing intermolecular interaction energies from energy frameworks analysis, slip layer topology, Hirshfeld surface analysis, and nanoindentation. The quantitative nanoindentation studies unveiled that Form III has higher elastic modulus and stiffness than Forms I and II, while the hardness was lowest for the plastic Form II. Despite high structural similarity in Forms II (plastic) and III (elastic), the E of elastic Form III was found to be 3 orders of magnitude higher than that of plastic Form II crystals, which is attributed to the subtle differences in interaction energies and slip layer topology in the two cases. Consideration of slip layer topology and interaction energies from the structures are very useful for rationalizing mechanical properties, but may not be always sufficient, and one may also need to know the topology of the potential energy surface of the slip layers for understanding the distinct mechanical behavior.
Combretastatin A-4: The Antitubulin Agent that Inspired the Design and Synthesis of Styrene and Spiroisatin Hybrids as Promising Cytotoxic, Antifungal and Antiviral Compounds
Betancur-Galvis, Liliana,Brand, Yaneth M.,Casta?o, Verónica T.,Kouznetsov, Vladimir V.,Linares, Vicky C. R.,Puerto, Carlos E.
, p. 999 - 1010 (2020/10/14)
The design of a series of styrene and spiroisatin hybrids was based on the structure of combretastatin A-4 1. This library of 20 compounds were synthesized with the pharmacophoric units: 3,4,5-trimethoxy or/and 4-hydroxy-3-methoxy phenyl moities in their structure. Thereby, the libraries of β-nitrostyrenes 10a-10c, spiroisatin-dihydroquinolines 14a-14c, spiroisatinthiazolidinones 17a-17c and spiroisatin-nitropyrrolizidines 20a-20k were evaluated for their in vitro cytotoxic, anti-proliferative, antifungal and antiviral activities. Biological results revealed that among these compounds, β-nitrostyrenes 10a-10c exhibited significant cytotoxicity (HeLa and Jurkat tumor cells) and antifungal (T. mentagrophytes) activities. Moreover, the spiroisatin-dihydroquinoline 14a and 14c showed promising cytotoxicity (U937 cells). 14a-14c molecules were active against human herpesviruses serotypes 1 and 2 (HHV-1 and HHV-2), but only 14a and 14b were effective against dengue virus serotype 2 (DENV-2). The spiroisatin-nitropyrrolizidine 20c exhibited moderate anti-herpetic activity, while 17c spiroisatin-thiazolidinone derivative also reduced the infection of HHV-1 and DENV-2. Finally, the molecular docking showed that these kind of molecules interact with the subunit α/β-tubulin.
Preparation and antiplasmodial activity of 3',4'-dihydro-1'H-spiro(indoline-3,2'-quinolin)-2-ones
Mathebula, Bakolise,Butsi, Kamogelo Rosinah,van Zyl, Robyn Lynne,Jansen van Vuuren, Natasha Colleen,Hoppe, Heinrich Carl,Michael, Joseph Philip,de Koning, Charles Bernard,Rousseau, Amanda Louise
, p. 1849 - 1858 (2019/08/30)
A series of 3',4'-dihydro-1'H-spiro(indoline-3,2'-quinolin)-2-ones were prepared by the inverse-electron-demand aza-Diels–Alder reaction (Povarov reaction) of imines derived from isatin and substituted anilines, and the electron-rich alkenes trans-isoeuge
