New route for synthesis of 2-(2,2-dimethoxyethyl)-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b]indole and DFT investigation

Uludag, Nesimi; Serdaroğlu, Goncagül

doi:10.1016/j.heliyon.2020.e04105

Cited by 9 publications

(5 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Due to the mainly sp 2 Here, the calculated NMR shifts were calculated greater than the relevant recorded data, as expected from the literature. [74][75] Results obtained from the NMR study give further support to the binding mode discussed in IR spectra.…”

Section: Nmr Spectral Studysupporting

confidence: 56%

“…The band observed at 3135 cm À 1 was assigned as NÀ H elongation mode at 3422 cm À 1 . Recently, the υNH elongation band for primary and secondary amines was observed in ∼ 3500-3300 cm À 1 , [76] and reported by theoretical calculations at 3300-3500 cm À 1 , [73][74][75]77] respectively. Also, υN=C vibrations for the azomethine and thiazole ring of compound 3 were assigned at 1618, 1598, 1213 cm À 1 , and 1495 and 1440 cm À 1 , respectively.…”

Section: Ft-ir Spectral Studymentioning

confidence: 89%

“…NBO method provides essential information of the molecular systems considering the intra-molecular interactions such as resonance, hyperconjugative, anomeric, etc. In this context, there have been reported [72][73][74][75][85][86][87][88] a lot of works from the simple-organic systems to complex molecules that evaluated the chemical stability, reactivity, and polarizability via using the NBOs approaches and the second-order perturbative energy analysis.…”

Section: Nbo Studymentioning

confidence: 99%

See 2 more Smart Citations

New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

Erdoğan

Serdaroğlu

2021

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

A novel pyrene-sulfathiazole-based potential drug candidate 3 was designed, successfully synthesized by a condensation reaction of pyrenecarboxaldehyde (1) with sulfathiazole (2) in good yield, and fully characterized by NMR, IR, UV-Vis, and HRMS spectroscopic techniques. The TD-DFT/B3LYP calculations displayed that the recorded peaks at 396, 377, 280, and 236 nm were due to the mainly n-π* and partially π-π* transitions that occurred on pyrene, azomethine, and sulfathiazole moieties. The NBO results disclosed that the electron delocalizations happened onto sulfathiazole, aromatic rings (pyrene and Ph-), and azomethine groups had the main responsibility of the lowering stabilization energy of compound 3. The NMR shifts were calculated by using the GIAO approaches in the DMSO phase and compared with the relevant data recorded. The thermodynamic and quantum chemical quantities were used for elucidating the physicochemical properties and reactivity behavior, in THF, DMSO, and water simulation environments. Accordingly, the calculated DM (D) and α (au) order of compound 3 were calculated in the order of vacuum < THF < DMSO < water, which indicated that the stability and thus reactivity of the compound strongly depended on the solvent environment. The FMO studies implied that the electron-donating possibility of compound 3 was dominant to the electron-accepting potency. In this work, the SMD version of IEFPCM was used in solvent media simulations.

show abstract

Section: Nmr Spectral Studysupporting

confidence: 56%

Section: Ft-ir Spectral Studymentioning

confidence: 89%

Section: Nbo Studymentioning

confidence: 99%

See 1 more Smart Citation

New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

Erdoğan

Serdaroğlu

2021

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

show abstract

“…A rather large number of synthetic pathways have been developed for the construction of the azocino [4,3-b]indole skeleton so far. [17][18][19][20][21][22][23] In our study, an alternative synthetic entry to the tetracyclic ring system of strychnos alkaloid is presented. We envisaged to develop an alternative strategy to reach the tetracyclic compound 7.…”

Section: Introductionmentioning

confidence: 99%

A simple and efficient method for constructing azocino[4,3-b]indole

Uludag¹

2022

Maced. J. Chem. Chem. Eng.

View full text Add to dashboard Cite

A new synthetic procedure has been developed to prepare the biologically important azocino[4,3-b]indole via the tetrafluoro-1,4-benzoquinone (TFB)-mediated cyclization of a tetrahydrocarbazole derivative bearing an amide side chain at the C-2 position. For the first time, this strategy is based on a different method for the C-2 position of the tetrahydrocarbazole for the synthesis of methanoazocino[4,3-b]indole. The notable features of this protocol include its operational simplicity and high reaction yields. Furthermore, the structures of all the presently synthesized compounds were confirmed using spectroscopic methods (1H NMR, 13C NMR, FT-IR).

show abstract

“…Hence, the aqueous chemistry of valuable active materials is imperative. Several DFT researches have been reported on the interactions of H 2 O with cluster systems [ 36 , 37 , 38 , 39 , 40 , 41 ].…”

Section: Introductionmentioning

confidence: 99%

Understanding the aqueous chemistry of quinoline and the diazanaphthalenes: insight from DFT study

Enudi

Louis

Edim

et al. 2021

Heliyon

View full text Add to dashboard Cite

The inter-fragment interactions at various binding sites and the overall cluster stability of quinolone (QNOL), cinnoline (CNOL), quinazoline (QNAZ), and quinoxaline (QNOX) complexes with H 2 O were studied using the density functional theory (DFT) approach. The adsorption and H-bond binding energies, and the energy decomposition mechanism was considered to determine the relative stabilization status of the studied clusters. Scanning tunneling microscopy (STM), natural bonding orbitals (NBO) and charge decomposition were studied to expose the electronic distribution and interaction between fragments. The feasibility of formations of the various complexes were also studied by considering their thermodynamic properties. Results from adsorption studies confirmed the actual adsorption of H 2 O molecules on the various binding sites studied, with QNOX clusters exhibiting the best adsorptions. Charge decomposition analysis (CDA) revealed significant charge transfer from substrate to H 2 O fragment in most complexes, except in QNOL, CNOL and QNAZ clusters with H 2 O at binding position 4, where much charges are back-donated to substrate. The O-H inter-fragment bonds was discovered to be stronger than counterpart N-H bonds in the complexes, whilst polarity indices confirmed N-H as more polar covalent than O-H bonds. Thermodynamic considerations revealed that the formation process of all studied complexes are endothermic (þve ΔH f ) and non-spontaneous (þve ΔG f ).

show abstract

New route for synthesis of 2-(2,2-dimethoxyethyl)-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b]indole and DFT investigation

Cited by 9 publications

References 45 publications

New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

A simple and efficient method for constructing azocino[4,3-b]indole

Understanding the aqueous chemistry of quinoline and the diazanaphthalenes: insight from DFT study

Contact Info

Product

Resources

About