Ethyl 2-[(4-chlorophenyl)hydrazono]-3-oxobutanoate

Fun, Hoong‐Kun; Chantrapromma, Suchada; Padaki, Mahesh; Radhika, .; Isloor, Arun M.

doi:10.1107/s1600536809012951

Cited by 3 publications

(6 citation statements)

References 7 publications

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“…The intramolecular N1-H1•••O1 hydrogen bond generates an S(6) ring motif (Bernstein et al, 1995) (Table 1). The bond distances in (II) have normal values (Allen et al, 1987) and are comparable to those in closely related structures (Alpaslan et al, 2005a, b;Fun et al, 2009).…”

Section: Methodssupporting

confidence: 69%

“…Some oxobutanoate derviatives exhibit cytotoxicity (Stancho et al, 2008). We previously reported the crystal structure of the ethyl 2-[(4-chlorophenyl)hydrazono]-3-oxobutanoate (I) (Fun et al, 2009). As part of our on going research on the synthesis and biological activity of oxobutanoates, we report here the synthesis and crystal structure of…”

Section: Methodsmentioning

confidence: 99%

“…The aromatic ring and aliphatic chain have a trans configuration with respect to the N-N bond as evidenced by the torsion angle C6-N1-N2-C7 being 179.76 (15)°. The orientations of 3-oxobutanoate and ethyl group are determined by the torsion angles C10-C7-C8-C9 = 3.3 (3)° and C10-O2-C11-C12 = 168.38 (10)° [the corresponding angles are 2.81 (15)° and 170.6 (9)° in (I) (Fun et al, 2009)]. The intramolecular N1-H1•••O1 hydrogen bond generates an S(6) ring motif (Bernstein et al, 1995) (Table 1).…”

Section: Methodsmentioning

confidence: 99%

“…For background to the bioactivity and applications of oxobutanoate derivatives, see: Alpaslan et al (2005a,b); Stancho et al (2008). For related structures, see: Alpaslan et al (2005a,b); Fun et al (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986).…”

Section: Related Literaturementioning

confidence: 99%

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Ethyl 2-[(3-chlorophenyl)hydrazono]-3-oxobutanoate

et al. 2009

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The molecule of the title oxobutanoate derivative, C12H13ClN2O3, adopts a keto–hydrazo tautomeric form and is roughly planar, the angle between the benzene ring and the mean plane through the hydrazone and aliphatic chain being 1.49 (6)°. This planarity is further aided by the formation of an intramolecular N—H⋯O hydrogen bond which generates an S(6) ring motif. The aromatic ring and aliphatic chain have a trans configuration with respect to the N—N bond. In the crystal packing, centrosymmetric R 2 2(16) dimers are formed through pairs of weak C—H⋯O(3-oxo) interactions. These dimers are linked together through weak C—H⋯O(carboxylate C=O) interactions into ribbons along the b-axis direction. These ribbons are stacked along the a-axis direction. The crystal also exhibits Cl⋯Cl [3.4988 (6) Å] and C⋯O [3.167 (2)–3.335 (2) Å] short contacts.

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Section: Methodssupporting

confidence: 69%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Related Literaturementioning

confidence: 99%

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Ethyl 2-[(3-chlorophenyl)hydrazono]-3-oxobutanoate

et al. 2009

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“…For details of the isolation and cytotoxic properties of oxobutanoate derivatives, see: Billington et al (1979); Stanchev et al (2008). For related structures, see: Alpaslan et al (2005); Fun et al (2009). For details of the synthesis, see: Amir & Agarwal, (1997).…”

Section: Related Literaturementioning

confidence: 99%

Ethyl 2-[(2,6-dimethylphenyl)hydrazono]-3-oxobutanoate

et al. 2009

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The title compound, C14H18N2O3, crystallizes with two independent molecules in the asymmetric unit, having closely comparable geometries. Both molecules are essentially planar [maximum deviations from the mean plane of 0.069 (1) and 0.068 (1) Å for the two molecules] and contain an intramolecular N—H⋯O hydrogen bond which generates a ring with graph-set motif S(6). In the crystal, the molecules are linked into chains along the c axis by intermolecular C—H⋯O hydrogen bonds, and intermolecular C—H⋯π interactions are also present.

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Design and synthesis of small molecule-sulfotyrosine mimetics that inhibit HIV-1 entry

Dogo‐Isonagie

Su-Lin

Lohith

et al. 2016

Bioorganic & Medicinal Chemistry

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In the absence of a cure or vaccine for HIV/AIDS, small molecule inhibitors remain an attractive choice for antiviral therapeutics. Recent structural and functional studies of the HIV-1 surface envelope glycoprotein gp120 have revealed sites of vulnerability that can be targeted by small molecule and peptide inhibitors, thereby inhibiting HIV-1 infection. Here we describe a series of small molecule entry inhibitors that were designed to mimic the sulfated N-terminal peptide of the HIV-1 coreceptor CCR5. From a panel of hydrazonothiazolyl pyrazolinones, we demonstrate that compounds containing naphthyl di- and tri-sulfonic acids inhibit HIV-1 infection in single round infectivity assays with the disulfonic acids being the most potent. Molecular docking supports the observed structure activity relationship, and SPR confirmed binding to gp120. In infectivity assays treatment with a representative naphthyl disulfonate and a disulfated CCR5 N-terminus peptide results in competitive inhibition, with combination indices >2. In total this work shows that gp120 and HIV-1 infection can be inhibited by small molecules that mimic the function of, and are competitive with the natural sulfated CCR5 N-terminus.

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Ethyl 2-[(4-chlorophenyl)hydrazono]-3-oxobutanoate

Cited by 3 publications

References 7 publications

Ethyl 2-[(3-chlorophenyl)hydrazono]-3-oxobutanoate

Ethyl 2-[(3-chlorophenyl)hydrazono]-3-oxobutanoate

Ethyl 2-[(2,6-dimethylphenyl)hydrazono]-3-oxobutanoate

Design and synthesis of small molecule-sulfotyrosine mimetics that inhibit HIV-1 entry

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