A new [2 + 2] photodimerization of 5-chloro- and 5-methyl-2-pyridone in their inclusion complexes with 1,1′-biphenyl-2,2′-dicarboxylic acid as a model for DNA damage by photodimerization of its thymine component

Hirano, Shinya; Toyota, Shinji; Toda, Fumio

doi:10.1039/b414134b

Cited by 15 publications

(6 citation statements)

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“…We also reported [4+4] photodimerizations of 2‐pyridone itself ( 1 c ) and 1 b in their inclusion complexes with 2 and a 1,2,4,5‐benzenetetracarboxylic acid host ( 4 ), respectively, which give the rac ‐ trans ‐ anti dimer 5 c and the meso ‐ cis ‐ syn dimer 6 b , respectively 3. 4 X‐ray analyses of these inclusion complexes showed that the 2‐pyridone molecules are ordered at reasonable positions for the corresponding photodimerization reactions in all cases 2–4…”

Section: Methodsmentioning

confidence: 95%

“…Efficient and selective inter‐ and intramolecular photoreactions of guest compounds in their inclusion complexes with a host compound have long been studied 1. We reported that photoirradiation of a 1:2 inclusion complex of 5‐methyl‐ ( 1 a ) and 5‐chloro‐2‐pyridone ( 1 b ) with a 2,2′‐biphenyldicarboxylic acid host ( 2 ) gives the corresponding rac‐cis‐anti dimer 3 a and 3 b , respectively 2. 3 These [2+2] photodimerization reactions of 2‐pyridone derivatives are important as models for DNA damage; this damage occurs by photodimerization of the thymine component of DNA, which is the cause of skin cancer.…”

Section: Methodsmentioning

confidence: 99%

“…Heating of the thermally labile 6 a as 10 in CD 3 COOD at 70 °C for 2 h gave 11 in quantitative yield. The structure of 11 was elucidated by comparison of its 1 H and 13 C NMR spectra with those of 3 a 2. 3 The meso ‐ cis ‐ syn dimer 11 is the first example of a [2+2] photodimer of 2‐pyridone that has a cis ‐ syn configuration.…”

Section: Methodsmentioning

confidence: 99%

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Solid‐State Phase Transition of an Inclusion Complex of 5‐Methyl‐2‐pyridone with 1,3,5‐Benzenetricarboxylic Acid

et al. 2006

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Section: Methodsmentioning

confidence: 95%

Section: Methodsmentioning

confidence: 99%

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Solid‐State Phase Transition of an Inclusion Complex of 5‐Methyl‐2‐pyridone with 1,3,5‐Benzenetricarboxylic Acid

et al. 2006

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“…This behavior might be attributed to the mutual orientation, namely head-to-head with the methyl groups overlapping each other. It is important to note, however, that irradiation of solid inclusion compounds of diphenic acid with 5-chloro-or 5-methyl-2-pyridone revealed [2+2] photodimerization to the corresponding cis-anti dimer (Hirano et al, 2005). However, in the later, the distances between the reacting atoms were very short (3.458 and 3.458 Å ) and the methyl groups did not overlap each other.…”

Section: Figurementioning

confidence: 97%

Structural effects on the solid-state photodimerization of 2-pyridone derivatives in inclusion compounds

Telzhensky

Kaftory

2009

Acta Crystallogr C

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The structures of six crystalline inclusion compounds between various host molecules and three guest molecules based on the 2-pyridone skeleton are described. The six compounds are 1,1'-biphenyl-2,2'-dicarboxylic acid-2-pyridone (1/2), C(14)H(10)O(4).2C(5)H(5)NO, (I-a), 1,1'-biphenyl-2,2'-dicarboxylic acid-4-methyl-2-pyridone (1/2), C(14)H(10)O(4).2C(6)H(7)NO, (I-c), 1,1'-biphenyl-2,2'-dicarboxylic acid-6-methyl-2-pyridone (1/2), C(14)H(10)O(4).2C(6)H(7)NO, (I-d), 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol-1-methyl-2-pyridone (1/2), C(30)H(22)O(2).2C(6)H(7)NO, (II-b), 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6-diol-4-methy-2-pyridone (1/2), C(30)H(22)O(2).2C(6)H(7)NO, (II-c), and 4,4',4''-(ethane-1,1,1-triyl)triphenol-6-methyl-2-pyridone-water (1/3/1), C(20)H(18)O(3).3C(6)H(7)NO.H(2)O, (III-d). In two of the compounds, (I-a) and (I-d), the host molecules lie about crystallographic twofold axes. In two other compounds, (II-b) and (II-c), the host molecules lie across inversion centers. In all cases, the guest molecules are hydrogen bonded to the host molecules through O-H...O=C hydrogen bonds [the range of O...O distances is 2.543 (2)-2.843 (2) A. The pyridone moieties form dimers through N-H...O=C hydrogen bonds in five of the compounds [the range of N...O distances is 2.763 (2)-2.968 (2) A]. In four compounds, (I-a), (I-c), (I-d) and (II-c), the molecules are arranged in extended zigzag chains formed via host-guest hydrogen bonding. In five of the compounds, the guest molecules are arranged in parallel pairs on top of each other, related by inversion centers. However, none of these compounds underwent photodimerization in the solid state upon irradiation. In one of the crystalline compounds, (III-d), the guest molecules are arranged in stacks with one disordered molecule. The unsuccessful dimerization is attributed to the large interatomic distances between the potentially reactive atoms [the range of distances is 4.027 (4)-4.865 (4) A] and to the bad overlap, expressed by the lateral shift between the orbitals of these atoms [the range of the shifts from perfect overlap is 1.727 (4)-3.324 (4) A]. The bad overlap and large distances between potentially photoreactive atoms are attributed to the hydrogen-bonding schemes, because the interactions involved in hydrogen bonding are stronger than those in pi-pi interactions.

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“…The crystal structures of neat 5-chloro-2(1H)-pyridone (1) (refcode CLPYRO [29] in the Cambridge Crystallographic Data Center CCDC [30]) as well as its molecular compounds with three different host molecules: with 1,2,4,5-benzenetetracarboxylic acid (III-1) (refcode FEHWEB [31]), with 1,1 0 -biphenyl-2,2 0 -dicarboxylic acid (VI-1) (refcode FEWSEG [32]) and with adipic acid (VII-1) (refcode XASDEA [33]) are known. In the neat compound (1) the molecules adopt the herring-bone packing mode.…”

Section: Resultsmentioning

confidence: 99%

Structural effects on the solid-state photodimerization of 5-chloro and 5-nitro-2(1H)-pyridone in molecular compounds

et al. 2011

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The preparation and crystal structure of six molecular compounds consist of light-stable host molecules [(1-cyclohexyl-4-hydroxybenzene, 1,1,6,6-tetrapheny l-2,4-hexadiyne-1,6-diol, 4-((10-[4-(ethoxycarbonyl)phenoxy]decyl)oxy)benzene, 1,2,4,5-benzenetetracarboxylic acid, resorcinol] and light-sensitive guest molecules [(5-chloro-2(1H)-pyridone or 5-nitro-2(1H)-pyridone] are described in light of their failure to undergo [4 ? 4] photodimerization in the solid-state upon irradiation with UV light. Unlike in many cases were pyridone and its derivatives undergo such dimerization in the solid-state due to the packing arrangement in the crystalline form in which the geometric requirement for photodimerization meet, the compounds described here failed to pack in ways to enable such photodimerization. The distances between the potentially reactive atoms ranged from 4.620 to 8.408 Å which are too long to react.

show abstract

A new [2 + 2] photodimerization of 5-chloro- and 5-methyl-2-pyridone in their inclusion complexes with 1,1′-biphenyl-2,2′-dicarboxylic acid as a model for DNA damage by photodimerization of its thymine component

Cited by 15 publications

References 7 publications

Solid‐State Phase Transition of an Inclusion Complex of 5‐Methyl‐2‐pyridone with 1,3,5‐Benzenetricarboxylic Acid

Solid‐State Phase Transition of an Inclusion Complex of 5‐Methyl‐2‐pyridone with 1,3,5‐Benzenetricarboxylic Acid

Structural effects on the solid-state photodimerization of 2-pyridone derivatives in inclusion compounds

Structural effects on the solid-state photodimerization of 5-chloro and 5-nitro-2(1H)-pyridone in molecular compounds

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