The crystal structures determination and Hirshfeld surface analysis of -(4-bromo-3-meth-oxy-phen-yl)- and -{[3-bromo-1-(phenyl-sulfon-yl)-1-indol-2-yl]meth-yl}- derivatives of -{[3-bromo-1-(phenylsulfon-yl)-1-indol-2-yl]meth-yl}benzene-sulfonamide.

Two new phenyl-sulfonyl-indole derivatives, namely, -{[3-bromo-1-(phenyl-sulfon-yl)-1-indol-2-yl]meth-yl}--(4-bromo-3-meth-oxy-phen-yl)benzene-sulfonamide, CHBrNOS, (), and ,-bis-{[3-bromo-1-(phenyl-sulfon-yl)-1-indol-2-yl]meth-yl}benzene-sulfonamide, CHBrNOS, (), reveal the impact of intra-molecular π-π inter-actions of the indole moieties as a factor not only governing the conformation of ,-bis-(1-indol-2-yl)meth-yl)amines, but also significantly influencing the crystal patterns. For , the crystal packing is dominated by C-H⋯π and π-π bonding, with a particular significance of mutual indole-indole inter-actions. In the case of , the mol-ecules adopt short intra-molecular π-π inter-actions between two nearly parallel indole ring systems [with the centroids of their pyrrole rings separated by 3.

Synthesis of di/tri-substituted carbazoles involving Pd-mediated Sonogashira coupling of indolyltriflates with aryl acetylenes.

In this study, we present our preliminary findings on the synthesis of carbazole derivatives involving the Sonogashira coupling reaction of 2-(trimethylamino)methylindolyltriflates with aryl acetylenes followed by isomerization, thermal electrocyclization and 1,3-H shift, furnishing the respective di- and tri-substituted carbazoles.

Crystal structure and Hirshfeld surface analysis of ()--(2-styrylphen-yl)benzene-sulfonamide.

The crystal structure of the title compound CHNOS features hydrogen-bonding and C-H⋯π inter-actions. Hirshfeld surface analysis revealed that H⋯H, C⋯H/H⋯C and O⋯H/H⋯O inter-actions make a major contribution to the crystal packing. Docking studies were carried out to determine the binding affinity and inter-action profile of the title compound with EGFR kinase, a member of the ErbB family of receptor tyrosine kinases, which is crucial for processes such as cell proliferation and differentiation.

Synthesis of Indolo[2,3/3,2-]quinoline through Complementary PIDA/BF·OEt as Well as Pd(0)-Mediated Intramolecular Cyclization of Isomeric -((Aryl)--(phenylsulfonyl)indolyl)methylbenzenesulfonamides.

Herein, a straightforward facile synthesis of indolo[2,3-]quinoline analogues was reported from 2-arylamino(phenylsulfonyl)methylindoles involving PIDA/BF·OEt-mediated intramolecular dehydrogenative coupling (IDC) as a key step. Even though isomeric 3-arylamino(phenylsulfonyl)methylindoles, upon interaction with PIDA/BF·OEt, led to complications, synthesis of the indolo[3,2-]quinoline framework could be easily achieved from -(2-iodoaryl)--indolylmethylbenzenesulfonamide by employing a Pd(0)-mediated intramolecular cyclization reaction. Under identical conditions, synthesis of indolo[2,3-]quinolines was also accomplished from the respective -(2-iodoaryl)--indolylmethylbenzenesulfonamides.

Crystal structure determination and Hirshfeld surface analysis of -acetyl--3-meth-oxy-phenyl and -(2,5-di-meth-oxy-phen-yl)--phenyl-sulfonyl derivatives of -[1-(phenyl-sulfon-yl)-1-indol-2-yl]methanamine.

Two new [1-(phenyl-sulfon-yl)-1-indol-2-yl]methanamine derivatives, namely, -(3-meth-oxy-phen-yl)--{[1-(phenyl-sulfon-yl)-1-indol-2-yl]meth-yl}acetamide, CHNOS, (), and -(2,5-di-meth-oxy-phen-yl)--{[1-(phenyl-sulfon-yl)-1-indol-2-yl]meth-yl}benzene-sulfonamide, CHNOS, (), reveal a nearly orthogonal orientation of their indole ring systems and sulfonyl-bound phenyl rings. The sulfonyl moieties adopt the anti-periplanar conformation. For both compounds, the crystal packing is dominated by C-H⋯O bonding [C⋯O = 3.

Synthesis of α-, β-, and γ-Carbolines via Intramolecular Cyclization of Azidomethyl(indolyl)acrylates Involving PIFA-BF·OEt/DBU-Mediated Cyclization as well as Thermolysis Approaches.

In this study, we present our findings on the synthesis of α-, β-, γ-carbolines via PIFA/BF·OEt-mediated intramolecular cyclization of isomeric azidomethyl(indolyl)acrylates. Alternately, 1,5,7-triazabicyclo[4.4.

The crystal structures and Hirshfeld surface analysis of three new bromo-substituted 3-methyl-1-(phenyl-sulfon-yl)-1-indole derivatives.

Three new 1-indole derivatives, namely, 2-(bromo-meth-yl)-3-methyl-1-(phenyl-sulfon-yl)-1-indole, CHBrNOS, (), 2-[()-2-(2-bromo-5-meth-oxy-phen-yl)ethen-yl]-3-methyl-1-(phenyl-sulfon-yl)-1-indole, CHBrNOS, (), and 2-[()-2-(2-bromo-phen-yl)ethen-yl]-3-methyl-1-(phenyl-sulfon-yl)-1-indole, CHBrNOS, (), exhibit nearly orthogonal orientations of their indole ring systems and sulfonyl-bound phenyl rings. Such conformations are favourable for inter-molecular bonding involving sets of slipped π-π inter-actions between the indole systems and mutual C-H⋯π hydrogen bonds, with the generation of two-dimensional monoperiodic patterns. The latter are found in all three structures, in the form of supra-molecular columns with every pair of successive mol-ecules related by inversion.

Crystal structure and Hirshfeld surface analysis of 3-(bromo-meth-yl)-2-[1,2-di-bromo-2-(6-nitro-benzo[][1,3]dioxol-5-yl)eth-yl]-1-(phenyl-sulfon-yl)-1-indole chloro-form 0.585-solvate.

The title indole derivative, CHBrNOS, crystallizes with a partial occupancy [0.585 (4)] CHCl solvent mol-ecule. The dihedral angles between the indole ring system and pendant nitro-benzodioxolane rings system and phenyl-sulfonyl ring are 4.

Crystal-structure determination and Hirshfeld surface analysis of two new thio-phene derivatives: ()--{2-[2-(benzo[]thio-phen-2-yl)ethen-yl]-5-fluoro-phen-yl}benzene-sulfonamide and ()--{2-[2-(benzo[]thio-phen-2-yl)ethen-yl]-5-fluoro-phen-yl}--(but-2-yn-1-yl)benzene-sulfonamide.

In the title compounds, CHFNOS () and CHFNOS (), the benzo-thio-phene rings are essentially planar with maximum deviations of 0.009 (1) and 0.001 (1) Å for the carbon and sulfur atom in compounds and , respectively.

The synthesis, crystal structure and Hirshfeld surface analysis of the thio-phene derivatives 5-(phenyl-sulfon-yl)-5,6-di-hydro-benzo[4,5]thieno[3,2-]phenanthridine and ()--{2-[2-(benzo[]thiophen-2-yl)ethenyl]phen-yl}--(prop-2-yn-1-yl)benzene-sulfonamide.

In both of the title compounds, CHNOS, (), and CHNOS, (), the benzo-thio-phene rings are essentially planar with maximum deviations of 0.026 (1) and -0.016 (1) Å for the carbon and sulfur atoms in compounds () and (), respectively.

A Formal (4 + 2) Cycloaddition of Phosphorus Ylides: Synthesis of Aromatic and Heteroaromatic 1,2-Diesters and Diones.

Heteroarylmethylenephosphorus ylides underwent Michael addition with alkynediones and alkynediesters, followed by intramolecular cyclization and elimination of triphenylphosphine oxide to afford 1,2-diaroylbenzenes and 1,2-alkoxycarbonylcarbo- and heterocycles. The analogous (4 + 2) cycloaddition led to the formation of 2,3-diaroylquinolines.

Design, crystal structure determination, molecular dynamic simulation and MMGBSA calculations of novel p38-alpha MAPK inhibitors for combating Alzheimer's disease.

The hallmark of the Alzheimer's disease (AD) is the accumulation of aggregated, misfolded proteins. The cause for this accumulation is increased production of misfolded proteins and impaired clearance of them. Amyloid aggregation and tau hyperphosphorylation are the two proteinopathies which accomplish deprivation of cell and tissue hemostasis during neuropathological process of the AD, as a result of which progressive neuronal degeneration and the loss of cognitive functions.

Pd(0)-Catalyzed Intramolecular Heck reaction of 2/3-Aryl(amino)methyl-3/2-bromoindoles: Syntheses of 3,4-Benzo[]-β-carbolines, Benzo[4,5]isothiazolo[2,3-]indole 5,5-Dioxides, and 1,2-Benzo[]-γ-carbolines.

One-pot synthesis of 3,4-benzo[]-β-carbolines was achieved from 2-aryl(tosylamino)methyl-3-bromoindoles via 10 mol % Pd(OAc)/PPh-mediated intramolecular Heck coupling using KCO as a base in DMF at 110 °C with concomitant aromatization through an elimination of tosylsulfinic acid. Under identical conditions, the isomeric 3-aryl(tosylamino)methyl-2-bromoindoles upon intramolecular Heck reaction furnished benzo[4,5]isothiazolo[2,3-]indole 5,5-dioxides instead of the expected γ-carbolines. However, synthesis of the expected γ-carboline framework, 3-tosyl-6,9-dihydro-1,2-benzo[]-γ-carbolines, could be achieved from 3-aryl(tosylamino)methyl-2-bromoindoles containing a mesitylene sulfonyl unit as a protecting group on the indole nitrogen.

Diels-Alder reaction of tetraarylcyclopentadienones with benzo[b]thiophene S,S-dioxides: an unprecedented de-oxygenation vs. sulfur dioxide extrusion.

Diels-Alder reaction of tetraarylcyclopentadienones with benzo[b]thiophene dioxides in xylenes at reflux led to the formation of tetra aryl-substituted dibenzothiophene as well as penta aryl-substituted benzene analogues depending on the influence of aryl substituents present on cyclopentadienones. The intermediate dihydrodibenzothiophene-dioxides underwent aromatization either through de-oxygenation or extrusion of sulfur dioxide to furnish substituted dibenzothiophenes or benzenes.

Divergent Synthesis and Evaluation of the in vitro Cytotoxicity Profiles of 3,4-Ethylenedioxythiophenyl-2-propen-1-one Analogues.

A new series of 3,4-ethylenedioxythiophene (EDOT)-appended propenones were prepared by condensation reaction and their in vitro cytotoxicity effects were evaluated against five human cancer cell lines. Preliminary structure-activity relationships of EDOT-incorporated 2-propenone derivatives were also established. The EDOT-appended enones demonstrated significant cytotoxicity against human cancer cell lines.

Novel isothiacalothrixin B analogues exhibit cytotoxic activity on human colon cancer cells in vitro by inducing irreversible DNA damage.

Preliminary cytotoxic analysis of sulphur containing isosteric analogues of calothrixin B identified the useful anti-tumour activity of thia/isothiacalothrixin B which necessitated it's biological evaluation in colon and lung cancer cell lines. The isothia analogues induced cytotoxicity of HCT116 in a time-dependent manner and inhibited the clonogenic survival of HCT116 and NCI-H460 cells in a dose-dependent manner comparable to the standard anti-cancer drug camptothecin. Herein employing flow cytometry, we demonstrate that isothiacalothrixin B analogues inhibited proliferation of colon cancer cells by the arrest of cells in S and G2/M phases over a period of 48 hours at a concentration of 5 μM.

Crystal structure of dimethyl 1-oxo-2,4-di-phenyl-1,2-dihydronaphthalene-2,3-di-carboxyl-ate.

In the title compound, CHO, a 1,2-di-hydro-naphthalene derivative, the cyclo-hexa-1,3-diene ring of the 1,2-di-hydro-naphthalene ring system adopts a half-chair conformation. The mean plane of the 1,2-di-hydro-napthalene ring system makes dihedral angles of 86.23 (6) and 64.

Diels-Alder Reaction of Isobenzofurans/Cyclopentadienones with Tetrathiafulvalene: Preparation of Naphthalene, Fluoranthene, and Fluorenone Derivatives.

Diels-Alder reaction of 1,3-diarylbenzo[c]furan/cyclopentadienone with TTF followed by triflic acid mediated cleavage of the resulting adducts led to the formation of the respective 1,4-diaryl substituted naphthalenes, fluoranthenes, and fluorenones. The photophysical properties of representative diaryl-substituted hydrocarbons are also reported.

Synthesis and Biological Evaluation of Calothrixins B and their Deoxygenated Analogues.

A series of calothrixin B (2) analogues bearing substituents at the 'E' ring and their corresponding deoxygenated quinocarbazoles lacking quinone unit were synthesized. The cytotoxicities of calothrixins 1, 2, and 15b-p and quinocarbazole analogues were investigated against nine cancer cell lines. The quinocarbazoles 21a and 25a inhibited the catalytic activity of human topoisomerase II.

Crystal structures of 1-benzene-sulfon-yl-2-methyl-3-(4-nitro-benzoyl)-2,3-di-hydro-1-indole and 1-benzene-sulfon-yl-2-methyl-3-[(thio-phen-2-yl)carbon-yl]-2,3-di-hydro-1-indole.

In the title indole derivatives, CHNOS, (I) and CHNOS, (II), the sulfonyl-bound phenyl rings are almost orthogonal to the indole ring system, subtending dihedral angles of 88.33 (10) and 87.58 (16)°, respectively.

Synthetic Utility of Arylmethylsulfones: Annulative π-Extension of Aromatics and Hetero-aromatics Involving Pd(0)-Catalyzed Heck Coupling Reactions.

A straightforward and general method for the synthesis of annulated thiophene, dibenzothiophene, and carbazoles analogues has been achieved involving alkylation of 2-bromo-1-(phenylsulfonylmethyl)arene/heteroarene with arylmethyl bromides/heteroarylmethyl bromides using t-BuOK as a base in DMF, followed by Pd(0)-mediated intramolecular Heck coupling in the presence of KCO in DMF at 80-140 °C. The attractive feature of this protocol is that a wide variety of π-conjugated heterocycles could be readily accessed by an appropriate choice of arylmethylsulfones and benzylic bromides.

Crystal structures of three 1-oxo-1,2-di-hydro-naphthalene derivatives: dimethyl 4-(4-meth-oxy-phen-yl)-2-(4-methyl-phen-yl)-1-oxo-1,2-di-hydro-naphthalene-2,3-di-carboxyl-ate, dimethyl 1-oxo-2-(pyren-4-yl)-4-(thio-phen-2-yl)-1,2-di-hydro-naphthalene-2,3-di-carboxyl-ate and ethyl 1-oxo-2-phenyl-2,4-bis-(thio-phen-2-yl)-1,2-di-hydro-naphthalene-3-carboxyl-ate.

In the title 1-oxo-1,2-di-hydro-naphthalene derivatives, CHO, (I), CHOS, (II), and CHOS, (III), the cyclo-hexa-1,3-diene rings of the 1,2-di-hydro-naphthalene ring systems adopt half-chair, boat and half-chair conformations, respectively. The carbonyl O atoms attached to the di-hydro-naphthalene ring systems are each significantly deviated from the mean plane of the 1,2-di-hydro-naphthalene ring system, by 0.6162 (12) Å in (I), 0.

Crystal structures of three carbazole derivatives: 12-ethyl-7-phenyl-sulfonyl-7-benzofuro[2,3-]carbazole, (1), 2-(4,5-dimeth-oxy-2-nitro-phen-yl)-4-hy-droxy-9-phenyl-sulfonyl-9-carbazole-3-carbaldehyde, (2), and 12-phenyl-7-phenyl-sulfonyl-7-benzofuro[2,3-]carbazole, (3).

The three title compounds, CHNOS, (1), CHNOS, (2), and CHNOS, (3), are carbazole derivatives, where (1) and (3) are heterocycle-containing carbazoles with a benzo-furan moiety fused to a carbazole unit. In (2), a di-meth-oxy-nitro-phenyl ring is attached to the carbazole moiety. In the three derivatives, a phenyl-sulfonyl group is attached to the N atom of the carbazole unit.