The Vitamin K Activity of Naphthoquinones

Fernholz, E.; Ansbacher, S.; MacPhillamy, H. B.

doi:10.1021/ja01859a052

Cited by 11 publications

(7 citation statements)

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“…1,4-NQ has been investigated using broadband rotational spectroscopy and computational methods. Characterisation of the rotational spectrum of the parent species, and the 13 C and 18 O isotopologues allowed determination of the heavy-atom substitution r s , semi-experimental r e SE and mass-dependent r m…”

Section: Discussionmentioning

confidence: 99%

“…Transitions corresponding to 13 C and 18 O isotopologues were observed at the expected shifts below the frequencies from the parent species (see example in Figure 2). Due to the presence of a C 2 symmetry axis in 1,4-NQ, there are only five distinct 13 C and one 18 O isotopologues. Each 13 C and 18 O isotopologue transition exhibited an intensity about twice the natural abundance of the corresponding isotope.…”

Section: Rotational Spectrummentioning

confidence: 94%

“…Due to the presence of a C 2 symmetry axis in 1,4-NQ, there are only five distinct 13 C and one 18 O isotopologues. Each 13 C and 18 O isotopologue transition exhibited an intensity about twice the natural abundance of the corresponding isotope. Isotopologue transitions were fit to the same Hamiltonian as the parent species, which yielded the experimental rotational constants of Table 2.…”

Section: Rotational Spectrummentioning

confidence: 99%

“…[2,14] Their toxicity is higher than that of naphthalene, [15] which is one of the most abundant PAHs in the atmosphere. [16,17] 1,4-naphthoquinone (1,4-NQ, see Figure 1) is the major structural component of vitamin K, [18] and has been found to strongly inhibit cancer cell growth. [19] It is a major scaffold to develop new compounds with tuned features, by modifying its structural and electronic properties.…”

Section: Introductionmentioning

confidence: 99%

“…1,4‐naphthoquinone (1,4‐NQ, see Figure 1) is the major structural component of vitamin K, [18] and has been found to strongly inhibit cancer cell growth [19] . It is a major scaffold to develop new compounds with tuned features, by modifying its structural and electronic properties.…”

Section: Introductionmentioning

confidence: 99%

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Structural Changes Induced by Quinones: High‐Resolution Microwave Study of 1,4‐Naphthoquinone

et al. 2020

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1,4-Naphthoquinone (1,4-NQ) is an important product of naphthalene oxidation, and it appears as a motif in many biologically active compounds. We have investigated the structure of 1,4-NQ using chirped-pulse Fourier transform microwave spectroscopy and quantum chemistry calculations. The rotational spectra of the parent species, and its 13 C and 18 O isotopologues were observed in natural abundance, and their spectroscopic parameters were obtained. This allowed the determination of the substitution r s , mass-weighted r m and semi-experimental r e SE structures of 1,4-NQ. The obtained structural parameters show that the quinone moiety mainly changes the structure of the benzene ring where it is inserted, modifying the CÀ C bonds to having predominantly single or double bond character. Furthermore, the molecular electrostatic surface potential reveals that the quinone ring becomes electron deficient while the benzene ring remains a nucleophile. The most electrophilic areas are the hydrogens attached to the double bond in the quinone ring. Knowledge of the nucleophilic and electrophilic areas in 1,4-NQ will help understanding its behaviour interacting with other molecules and guide modifications to tune its properties.

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Section: Discussionmentioning

confidence: 99%

Section: Rotational Spectrummentioning

confidence: 94%

Section: Rotational Spectrummentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Structural Changes Induced by Quinones: High‐Resolution Microwave Study of 1,4‐Naphthoquinone

et al. 2020

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The Intravenous Use of Vitamin K

Olwin¹

1941

JAMA

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TheClemmensen Reduction

Martin

2011

Organic Reactions

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The replacement of the oxygen atoms of the carbonyl group in an aldehyde or ketone by two hydrogen atoms through the use of amalgamated zinc and hydrochloric acid was first employed in 1913 by Clemmensen and is know as the Clemmensen method of reduction. The process has been applied to a large number of aldehydes and ketones as a step in the synthesis of polynuclear hydrocarbons and alkylated aromatic compounds. It has also played an important role in the elucidation of the structures of highly complex natural products. The wide use of this method has resulted in the development of several modifications of the original procedure.

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The Vitamin K Activity of Naphthoquinones

Cited by 11 publications

References 0 publications

Structural Changes Induced by Quinones: High‐Resolution Microwave Study of 1,4‐Naphthoquinone

Structural Changes Induced by Quinones: High‐Resolution Microwave Study of 1,4‐Naphthoquinone

The Intravenous Use of Vitamin K

TheClemmensen Reduction

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