View in EDS

Synthesis, characterization and cytotoxicity properties of new dichlorothiophene based nicotinonitrile derivatives.

Saved in:
Bibliographic Details
Title: Synthesis, characterization and cytotoxicity properties of new dichlorothiophene based nicotinonitrile derivatives.
Authors: Al-Masri, Eman1,2 (AUTHOR), Ali, Basem F.1,2 (AUTHOR) bfali@aabu.edu.jo, Al-Refai, Mahmoud1,2 (AUTHOR) mahmoud_alrefai@aabu.edu.jo, Salah, Lubna3 (AUTHOR), Ponseca Jr, Carlito S.4,5 (AUTHOR), Mansi, Iman A.6 (AUTHOR), Abu-Irmaileh, Bashaer7 (AUTHOR), Aljaar, Nayyef8 (AUTHOR), Geyer, Armin9 (AUTHOR), Shuaib, Ali10 (AUTHOR)
Source: Journal of Molecular Structure. Dec2025, Vol. 1347, pN.PAG-N.PAG. 1p.
Subjects: Cytotoxins, Antineoplastic agents, Inorganic compounds, Chemical synthesis, Pyridine derivatives, Cell lines
Abstract: • A new series of pyridine-carbonitriles is synthesized. • X-ray structural analysis of one derivative and crystal supramolecularity are studied. • Cytotoxicity of all derivatives was assessed against four cell lines. • Derivative 11 is considered a potential anticancer candidate. • Derivative 1 is a highly potent compound for the treatment of breast cancer. New pyridine-carbonitrile derivatives (1–16) were synthesized and characterized. Some of these derivatives, (7–9) and (15–16), were formed as minor products by decyanation of the corresponding pyridine-carbonitriles main product. By using various spectral techniques, IR, 1H and 13C NMR, 2D NMR (COSY, HSQC, and HMBC) experiments, and electrospray ionization high-resolution mass spectrometry (ESI-HRMS), structure have been proposed for all derivatives and, for derivative 10 , additionally confirmed by single crystal structural analysis. The molecular structure of 10 is composed of a central 2-methoxypyridine-3-carbonitrile ring with two substituents in positions 4 (furan-2-yl) and 6 (5-chlorothiophen-2-yl). Crystal structure is stabilized by C—H···O/N hydrogen bonding, π···π stacking, and by C—H···π interactions. The cytotoxicity of all derivatives was assessed against four cell lines, namely, normal skin fibroblast, K562 (leukemia), MCF7 (breast cancer) and HCT116 (colon cancer). Cytotoxicity analysis results revealed that compound 11 had moderate cytotoxicity toward the leukemia (K562) and breast cancer (MCF7) cell lines. An interesting result was obtained for compound 1 which was toxic toward normal skin fibroblasts but highly toxic toward the MCF7 cell lines, with a half maximal inhibitory concentration [IC 50 ] of 1.7 ± 0.3 µM and an IC 50 selectivity ratio of 19.3. Compound 1 inhibited skin fibroblasts by 8% at a concentration of 3 µM. The two compounds are considered potential candidates for anticancer drugs. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Molecular Structure is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
FullText Text:
  Availability: 0
Header DbId: egs
DbLabel: Engineering Source
An: 188289867
AccessLevel: 6
PubType: Academic Journal
PubTypeId: academicJournal
PreciseRelevancyScore: 0
IllustrationInfo
Items – Name: Title
  Label: Title
  Group: Ti
  Data: Synthesis, characterization and cytotoxicity properties of new dichlorothiophene based nicotinonitrile derivatives.
– Name: Author
  Label: Authors
  Group: Au
  Data: <searchLink fieldCode="AR" term="%22Al-Masri%2C+Eman%22">Al-Masri, Eman</searchLink><relatesTo>1,2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Ali%2C+Basem+F%2E%22">Ali, Basem F.</searchLink><relatesTo>1,2</relatesTo> (AUTHOR)<i> bfali@aabu.edu.jo</i><br /><searchLink fieldCode="AR" term="%22Al-Refai%2C+Mahmoud%22">Al-Refai, Mahmoud</searchLink><relatesTo>1,2</relatesTo> (AUTHOR)<i> mahmoud_alrefai@aabu.edu.jo</i><br /><searchLink fieldCode="AR" term="%22Salah%2C+Lubna%22">Salah, Lubna</searchLink><relatesTo>3</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Ponseca+Jr%2C+Carlito+S%2E%22">Ponseca Jr, Carlito S.</searchLink><relatesTo>4,5</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Mansi%2C+Iman+A%2E%22">Mansi, Iman A.</searchLink><relatesTo>6</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Abu-Irmaileh%2C+Bashaer%22">Abu-Irmaileh, Bashaer</searchLink><relatesTo>7</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Aljaar%2C+Nayyef%22">Aljaar, Nayyef</searchLink><relatesTo>8</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Geyer%2C+Armin%22">Geyer, Armin</searchLink><relatesTo>9</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Shuaib%2C+Ali%22">Shuaib, Ali</searchLink><relatesTo>10</relatesTo> (AUTHOR)
– Name: TitleSource
  Label: Source
  Group: Src
  Data: <searchLink fieldCode="JN" term="%22Journal+of+Molecular+Structure%22">Journal of Molecular Structure</searchLink>. Dec2025, Vol. 1347, pN.PAG-N.PAG. 1p.
– Name: Subject
  Label: Subjects
  Group: Su
  Data: <searchLink fieldCode="DE" term="%22Cytotoxins%22">Cytotoxins</searchLink><br /><searchLink fieldCode="DE" term="%22Antineoplastic+agents%22">Antineoplastic agents</searchLink><br /><searchLink fieldCode="DE" term="%22Inorganic+compounds%22">Inorganic compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+synthesis%22">Chemical synthesis</searchLink><br /><searchLink fieldCode="DE" term="%22Pyridine+derivatives%22">Pyridine derivatives</searchLink><br /><searchLink fieldCode="DE" term="%22Cell+lines%22">Cell lines</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: • A new series of pyridine-carbonitriles is synthesized. • X-ray structural analysis of one derivative and crystal supramolecularity are studied. • Cytotoxicity of all derivatives was assessed against four cell lines. • Derivative 11 is considered a potential anticancer candidate. • Derivative 1 is a highly potent compound for the treatment of breast cancer. New pyridine-carbonitrile derivatives (1–16) were synthesized and characterized. Some of these derivatives, (7–9) and (15–16), were formed as minor products by decyanation of the corresponding pyridine-carbonitriles main product. By using various spectral techniques, IR, 1H and 13C NMR, 2D NMR (COSY, HSQC, and HMBC) experiments, and electrospray ionization high-resolution mass spectrometry (ESI-HRMS), structure have been proposed for all derivatives and, for derivative 10 , additionally confirmed by single crystal structural analysis. The molecular structure of 10 is composed of a central 2-methoxypyridine-3-carbonitrile ring with two substituents in positions 4 (furan-2-yl) and 6 (5-chlorothiophen-2-yl). Crystal structure is stabilized by C—H···O/N hydrogen bonding, π···π stacking, and by C—H···π interactions. The cytotoxicity of all derivatives was assessed against four cell lines, namely, normal skin fibroblast, K562 (leukemia), MCF7 (breast cancer) and HCT116 (colon cancer). Cytotoxicity analysis results revealed that compound 11 had moderate cytotoxicity toward the leukemia (K562) and breast cancer (MCF7) cell lines. An interesting result was obtained for compound 1 which was toxic toward normal skin fibroblasts but highly toxic toward the MCF7 cell lines, with a half maximal inhibitory concentration [IC 50 ] of 1.7 ± 0.3 µM and an IC 50 selectivity ratio of 19.3. Compound 1 inhibited skin fibroblasts by 8% at a concentration of 3 µM. The two compounds are considered potential candidates for anticancer drugs. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Journal of Molecular Structure is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
PLink https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&db=egs&AN=188289867
RecordInfo BibRecord:
  BibEntity:
    Identifiers:
      – Type: doi
        Value: 10.1016/j.molstruc.2025.143250
    Languages:
      – Code: eng
        Text: English
    PhysicalDescription:
      Pagination:
        PageCount: 1
        StartPage: N.PAG
    Subjects:
      – SubjectFull: Cytotoxins
        Type: general
      – SubjectFull: Antineoplastic agents
        Type: general
      – SubjectFull: Inorganic compounds
        Type: general
      – SubjectFull: Chemical synthesis
        Type: general
      – SubjectFull: Pyridine derivatives
        Type: general
      – SubjectFull: Cell lines
        Type: general
    Titles:
      – TitleFull: Synthesis, characterization and cytotoxicity properties of new dichlorothiophene based nicotinonitrile derivatives.
        Type: main
  BibRelationships:
    HasContributorRelationships:
      – PersonEntity:
          Name:
            NameFull: Al-Masri, Eman
      – PersonEntity:
          Name:
            NameFull: Ali, Basem F.
      – PersonEntity:
          Name:
            NameFull: Al-Refai, Mahmoud
      – PersonEntity:
          Name:
            NameFull: Salah, Lubna
      – PersonEntity:
          Name:
            NameFull: Ponseca Jr, Carlito S.
      – PersonEntity:
          Name:
            NameFull: Mansi, Iman A.
      – PersonEntity:
          Name:
            NameFull: Abu-Irmaileh, Bashaer
      – PersonEntity:
          Name:
            NameFull: Aljaar, Nayyef
      – PersonEntity:
          Name:
            NameFull: Geyer, Armin
      – PersonEntity:
          Name:
            NameFull: Shuaib, Ali
    IsPartOfRelationships:
      – BibEntity:
          Dates:
            – D: 15
              M: 12
              Text: Dec2025
              Type: published
              Y: 2025
          Identifiers:
            – Type: issn-print
              Value: 00222860
          Numbering:
            – Type: volume
              Value: 1347
          Titles:
            – TitleFull: Journal of Molecular Structure
              Type: main
ResultId 1