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DOI :10.26650/IstanbulJPharm.2024.1449135   IUP :10.26650/IstanbulJPharm.2024.1449135    Tam Metin (PDF)

Synthesis, characterization, and crystal structure of a novel spirocyclic 2-indolinone bearing a 5-(trifluoromethyl)benzothiazoline moiety

Asu Büşra TemizerFiliz Betül KaynakNilgün Lütfiye Karalı

Background and Aims: Spirocyclic 2-indolinones are important and promising compounds because of their various biological activities in drug development studies. The main aim of this study is to determine spirocyclic, molecular and stereoisomeric structure of the new 5’-chloro-1’,7’-dimethyl-5-(trifluoromethyl)-3H-spiro[1,3-benzothiazole-2,3’-indole]-2’-one (4) and to examine the contribution of the trifluoromethyl group.

Methods: Compound 4 was synthesized from the reaction of 2-amino-4-(trifluoromethyl)benzenethiol with 5-chloro-1,7-dimethyl1H-indole-2,3-dione in ethanol. The purity and structure determination of compound 4 was carried out by elemental and spectral analyzes. The crystal structure of compound 4 was characterized by X-ray single crystal diffraction analysis method (SC-XRD). Additionally, compliance with Lipinski’s rule of 5 (RO5) and some pharmacokinetic parameters of compound 4 were evaluated using the Qikprop modüle (Schrödinger).

Results: The molecular structure of 4 was confirmed by elemental and spectral (IR, 1H NMR, 13C NMR-APT, HSQC-2D, HMBC2D and LCMS-APCI) data. The crystal, spirocyclic and stereoisomeric structure of compound 4 was elucidated by SC-XRD, and it was observed that N-H···O hydrogen bonding interactions take place within the molecular layers aligned parallel to the (010) plane. As a drug candidate, compound 4 exhibited physicochemical parameters consistent with Lipinski’s RO5.

Conclusion: In the crystal, both intra- and intermolecular hydrogen bonds are present. The molecular packing is stabilized by intermolecular N— H···O hydrogen bonds. 


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DIŞA AKTAR



APA

Temizer, A.B., Kaynak, F.B., & Karalı, N.L. (2024). Synthesis, characterization, and crystal structure of a novel spirocyclic 2-indolinone bearing a 5-(trifluoromethyl)benzothiazoline moiety. İstanbul Journal of Pharmacy, 54(3), 456-465. https://doi.org/10.26650/IstanbulJPharm.2024.1449135


AMA

Temizer A B, Kaynak F B, Karalı N L. Synthesis, characterization, and crystal structure of a novel spirocyclic 2-indolinone bearing a 5-(trifluoromethyl)benzothiazoline moiety. İstanbul Journal of Pharmacy. 2024;54(3):456-465. https://doi.org/10.26650/IstanbulJPharm.2024.1449135


ABNT

Temizer, A.B.; Kaynak, F.B.; Karalı, N.L. Synthesis, characterization, and crystal structure of a novel spirocyclic 2-indolinone bearing a 5-(trifluoromethyl)benzothiazoline moiety. İstanbul Journal of Pharmacy, [Publisher Location], v. 54, n. 3, p. 456-465, 2024.


Chicago: Author-Date Style

Temizer, Asu Büşra, and Filiz Betül Kaynak and Nilgün Lütfiye Karalı. 2024. “Synthesis, characterization, and crystal structure of a novel spirocyclic 2-indolinone bearing a 5-(trifluoromethyl)benzothiazoline moiety.” İstanbul Journal of Pharmacy 54, no. 3: 456-465. https://doi.org/10.26650/IstanbulJPharm.2024.1449135


Chicago: Humanities Style

Temizer, Asu Büşra, and Filiz Betül Kaynak and Nilgün Lütfiye Karalı. Synthesis, characterization, and crystal structure of a novel spirocyclic 2-indolinone bearing a 5-(trifluoromethyl)benzothiazoline moiety.” İstanbul Journal of Pharmacy 54, no. 3 (Mar. 2025): 456-465. https://doi.org/10.26650/IstanbulJPharm.2024.1449135


Harvard: Australian Style

Temizer, AB & Kaynak, FB & Karalı, NL 2024, 'Synthesis, characterization, and crystal structure of a novel spirocyclic 2-indolinone bearing a 5-(trifluoromethyl)benzothiazoline moiety', İstanbul Journal of Pharmacy, vol. 54, no. 3, pp. 456-465, viewed 14 Mar. 2025, https://doi.org/10.26650/IstanbulJPharm.2024.1449135


Harvard: Author-Date Style

Temizer, A.B. and Kaynak, F.B. and Karalı, N.L. (2024) ‘Synthesis, characterization, and crystal structure of a novel spirocyclic 2-indolinone bearing a 5-(trifluoromethyl)benzothiazoline moiety’, İstanbul Journal of Pharmacy, 54(3), pp. 456-465. https://doi.org/10.26650/IstanbulJPharm.2024.1449135 (14 Mar. 2025).


MLA

Temizer, Asu Büşra, and Filiz Betül Kaynak and Nilgün Lütfiye Karalı. Synthesis, characterization, and crystal structure of a novel spirocyclic 2-indolinone bearing a 5-(trifluoromethyl)benzothiazoline moiety.” İstanbul Journal of Pharmacy, vol. 54, no. 3, 2024, pp. 456-465. [Database Container], https://doi.org/10.26650/IstanbulJPharm.2024.1449135


Vancouver

Temizer AB, Kaynak FB, Karalı NL. Synthesis, characterization, and crystal structure of a novel spirocyclic 2-indolinone bearing a 5-(trifluoromethyl)benzothiazoline moiety. İstanbul Journal of Pharmacy [Internet]. 14 Mar. 2025 [cited 14 Mar. 2025];54(3):456-465. Available from: https://doi.org/10.26650/IstanbulJPharm.2024.1449135 doi: 10.26650/IstanbulJPharm.2024.1449135


ISNAD

Temizer, AsuBüşra - Kaynak, FilizBetül - Karalı, NilgünLütfiye. Synthesis, characterization, and crystal structure of a novel spirocyclic 2-indolinone bearing a 5-(trifluoromethyl)benzothiazoline moiety”. İstanbul Journal of Pharmacy 54/3 (Mar. 2025): 456-465. https://doi.org/10.26650/IstanbulJPharm.2024.1449135



ZAMAN ÇİZELGESİ


Gönderim08.03.2024
Kabul22.10.2024
Çevrimiçi Yayınlanma30.12.2024

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