Synthesis, anticancer, structural, and computational docking studies of 3-benzylchroman-4-one derivatives

Simon, Lalitha; Salam, Abdul Ajees Abdul; Kumar, Shankar; Shilpa, T.; Srinivasan, Kannupal; Byrappa, K.

doi:10.1016/j.bmcl.2017.10.026

Cited by 17 publications

(18 citation statements)

References 39 publications

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“…5b and Table S3 in the supporting information). There are slight variations in some structures due to torsion-angle variations and bulk substitution in the phenyl rings or at the N atom, which are common and have been observed in previously reported structures (Simon et al, 2017). For example, YEVSAT and FIBROY-Mol1 have methyl substitution at the 4-position in the phenyl rings.…”

Section: Figuresupporting

confidence: 53%

Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C₆H₅O)₂P(O)X [X = NHC₇H₁₃ and N(CH₂C₆H₅)₂]

et al. 2020

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The crystal structures of diphenyl (cycloheptylamido)phosphate, C19H24NO3P or (C6H5O)2P(O)(NHC7H13), (I), and diphenyl (dibenzylamido)phosphate, C26H24NO3P or (C6H5O)2P(O)[N(CH2C6H5)2], (II), are reported. The NHC7H13 group in (I) provides two significant hydrogen-donor sites in N—H...O and C—H...O hydrogen bonds, needed for a one-dimensional hydrogen-bond pattern along [100] in the crystal, while (II), with a (C6H5CH2)2N moiety, lacks these hydrogen bonds, but its three-dimensional supramolecular structure is mediated by C—H...π interactions. The conformational behaviour of the phenyl rings in (I), (II) and analogous structures from the Cambridge Structural Database (CSD) were studied in terms of flexibility, volume of the other group attached to phosphorus and packing forces. From this study, synclinal (±sc), anticlinal (±ac) and antiperiplanar (±ap) conformations were found to occur. In the structure of (II), there is an intramolecular C ortho —H...O interaction that imposes a +sc conformation for the phenyl ring involved. For the structures from the CSD, the +sc and ±ap conformations appear to be mainly imposed by similar C ortho —H...O intramolecular interactions. The large contribution of the C...H/H...C contacts (32.3%) in the two-dimensional fingerprint plots of (II) is a result of the C—H...π interactions. The differential scanning calorimetry (DSC) analyses exhibit peak temperatures (T m) at 109 and 81 °C for (I) and (II), respectively, which agree with the strengths of the intermolecular contacts and the melting points.

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Section: Figuresupporting

confidence: 53%

Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C₆H₅O)₂P(O)X [X = NHC₇H₁₃ and N(CH₂C₆H₅)₂]

et al. 2020

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“…The compound is known for human monoamine oxidase B inhibition [ 87 ]. Chromane scaffolds are promiscuous in NPs [ 67 ] and known for their anticancer activity [ 88 ] which may also be related with the database richness in anticancer compounds in Fig. 4 .…”

Section: Resultsmentioning

confidence: 99%

SANCDB: an update on South African natural compounds and their readily available analogs

et al. 2021

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Background South African Natural Compounds Database (SANCDB; https://sancdb.rubi.ru.ac.za/) is the sole and a fully referenced database of natural chemical compounds of South African biodiversity. It is freely available, and since its inception in 2015, the database has become an important resource to several studies. Its content has been: used as training data for machine learning models; incorporated to larger databases; and utilized in drug discovery studies for hit identifications. Description Here, we report the updated version of SANCDB. The new version includes 412 additional compounds that have been reported since 2015, giving a total of 1012 compounds in the database. Further, although natural products (NPs) are an important source of unique scaffolds, they have a major drawback due to their complex structure resulting in low synthetic feasibility in the laboratory. With this in mind, SANCDB is, now, updated to provide direct links to commercially available analogs from two major chemical databases namely Mcule and MolPort. To our knowledge, this feature is not available in other NP databases. Additionally, for easier access to information by users, the database and website interface were updated. The compounds are now downloadable in many different chemical formats. Conclusions The drug discovery process relies heavily on NPs due to their unique chemical organization. This has inspired the establishment of numerous NP chemical databases. With the emergence of newer chemoinformatic technologies, existing chemical databases require constant updates to facilitate information accessibility and integration by users. Besides increasing the NPs compound content, the updated SANCDB allows users to access the individual compounds (if available) or their analogs from commercial databases seamlessly. Graphic abstract

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“…L 2 was synthesized by following the method specified above for L 1 using 2,3,4-trihydroxybenzaldehyde (0.308 g, 2.0 mmol) instead of 4-phenylbenzaldehyde. Yellow colored crystals of L 2 were obtained in water and acetone mixture 1:1 (v/v) within 23…”

Section: Methodsmentioning

confidence: 99%

“…Like a deadly viral infection, cancer as well is a fearful disease recognized globally. It is the second leading cause of death worldwide . Many drugs that target cancer cells have a high degree of toxicity due to poor selectivity leads to potential side effect on human health.…”

Section: Introductionmentioning

confidence: 99%

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Design and Construction of Aroyl‐Hydrazone Derivatives: Synthesis, Crystal Structure, Molecular Docking and Their Biological Activities

Kumari

Ansari

Kumar

et al. 2019

Chemistry & Biodiversity

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Here, we report the synthesis and characterization of four new aroyl‐hydrazone derivatives L1–L4, and their structural as well as biological activities have been explored. In addition to docking with bovine serum albumin (BSA) and duplex DNA, the experimental results demonstrate the effective binding of L1–L4 with BSA protein and calf thymus DNA (ct‐DNA) which is in agreement with the docking results. Further biological activities of L1–L4 have been examined through molecular docking with different proteins which are involved in the propagation of viral or cancer diseases. L1 shows best binding affinity with influenza A virus polymerase PB2 subunit (2VY7) with binding energy −11.42 kcal/mol and inhibition constant 4.23 nm, whereas L2 strongly bind with the hepatitis C virus NS5B polymerase (2WCX) with binding energy −10.47 kcal/mol and inhibition constant 21.06 nm. Ligand L3 binds strongly with TGF‐beta receptor 1 (3FAA) and L4 with cancer‐related EphA2 protein kinases (1MQB) with binding energy −10.61 kcal/mol, −10.02 kcal/mol and inhibition constant 16.67 nm and 45.41 nm, respectively. The binding energies of L1–L4 are comparable with binding energies of their proven inhibitors. L1, L3 and L4 can be considered as both 3FAA and 1MQB dual targeting anticancer agents, while L1 and L3 are both 2VY7 and 2WCX dual targeting antiviral agents. On the other side, L2 and L4 target only one virus related target (2WCX). Furthermore, the geometry optimizations of L1–L4 were performed via density functional theory (DFT). Moreover, all four ligands (L1–L4) were characterized by NMR, FT‐IR, ESI‐MS, elemental analysis and their molecular structures were validated by single crystal X‐ray diffraction studies.

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Synthesis, anticancer, structural, and computational docking studies of 3-benzylchroman-4-one derivatives

Cited by 17 publications

References 39 publications

Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C₆H₅O)₂P(O)X [X = NHC₇H₁₃ and N(CH₂C₆H₅)₂]

Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C₆H₅O)₂P(O)X [X = NHC₇H₁₃ and N(CH₂C₆H₅)₂]

SANCDB: an update on South African natural compounds and their readily available analogs

Design and Construction of Aroyl‐Hydrazone Derivatives: Synthesis, Crystal Structure, Molecular Docking and Their Biological Activities

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Synthesis, anticancer, structural, and computational docking studies of 3-benzylchroman-4-one derivatives

Cited by 17 publications

References 39 publications

Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C6H5O)2P(O)X [X = NHC7H13 and N(CH2C6H5)2]

Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C6H5O)2P(O)X [X = NHC7H13 and N(CH2C6H5)2]

SANCDB: an update on South African natural compounds and their readily available analogs

Design and Construction of Aroyl‐Hydrazone Derivatives: Synthesis, Crystal Structure, Molecular Docking and Their Biological Activities

Contact Info

Product

Resources

About

Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C₆H₅O)₂P(O)X [X = NHC₇H₁₃ and N(CH₂C₆H₅)₂]

Conformational flexibility in amidophosphoesters: a CSD analysis completed with two new crystal structures of (C₆H₅O)₂P(O)X [X = NHC₇H₁₃ and N(CH₂C₆H₅)₂]