Structure of cinnamamide

Iwamoto, T.; Kashino, Setsuo; Haisa, M.

doi:10.1107/s0108270189002957

Cited by 7 publications

(3 citation statements)

References 2 publications

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“…The planarity, bond lengths and angles in the styryl fragment are comparable with previously reported values (Nilofar Nissa et al, 2002;Iwamoto et al, 1989). The widening of the C3-C4-C5 angle to 125.68 14has been previously attributed to intramolecular repulsion between C3 and C6 (Subramanian et al, 1999).…”

Section: Figuresupporting

confidence: 90%

Crystal structure determination as part of an ongoing undergraduate organic laboratory project: 5-[(E)-styryl]-1,3,4-oxathiazol-2-one

et al. 2017

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The title compound, C10H7NO2S, provides the first structure of an α-alkenyl oxathiazolone ring. The phenyl ring and the oxathiazolone groups make dihedral angles of 0.3 (3) and −2.8 (3)°, respectively, with the plane of the central alkene group; the dihedral angle between the rings is 2.68 (8)°. A careful consideration of bond lengths provides insight into the electronic structure and reactivity of the title compound. In the crystal, extended π-stacking is observed parallel to thea-axis direction, consisting of cofacial head-to-tail dimeric units [centroid–centroid distance of 3.6191 (11) Å]. These dimeric units are separated by a slightly longer centroid–centroid distance of 3.8383 (12) Å, generating infinite stacks of molecules.

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Section: Figuresupporting

confidence: 90%

Crystal structure determination as part of an ongoing undergraduate organic laboratory project: 5-[(E)-styryl]-1,3,4-oxathiazol-2-one

et al. 2017

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“…The cinnamide carbonyl oxygen is on the same side of the C-Cα bond as the double bond, which was observed in the crystal structure of several cinnamides. 38, 39 The double bond is slightly distorted because of collision between the carbonyl oxygen and the β-methyl group. This conformation was supported by 1 H ROESY NMR spectroscopy of the dipeptide mimic in DMSO- d 6 in which there was a strong cross peak between the Leu NH and the α-proton of the cinnamate.…”

Section: Resultsmentioning

confidence: 99%

Potent and Selective Phosphopeptide Mimetic Prodrugs Targeted to the Src Homology 2 (SH2) Domain of Signal Transducer and Activator of Transcription 3

et al. 2011

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Signal transducer and activator of transcription 3 (Stat3), a target for anticancer drug design, is activated by recruitment to phosphotyrosine residues on growth factor and cytokine receptors via its SH2 domain. We report here structure-activity relationship studies on phosphopeptide mimics targeted to the SH2 domain of Stat3. Inclusion of a methyl group on the β-position of the pTyr mimic, 4-phosphocinfnamide, enhanced affinity 2–3 fold. Bis-pivaloyloxymethyl prodrugs containing β-methyl cinnamide, dipeptide scaffolds Haic and Nle-cis-3,4-methanoproline, and glutamine surrogates were highly potent, completely inhibiting phosphorylation of Stat3 Tyr705 at 0.5–1 µM in a variety of cancer cell lines. The inhibitors were selective for Stat3 over Stat1, Stat5, Src, and p85 of PI3K, indicating ability to discriminate individual SH2 domains in intact cells. At concentrations that completely inhibited Stat3 phosphorylation, the prodrugs were not cytotoxic to a panel of tumor cells, thereby showing clear distinction between cytotoxicity and effects downstream of activated Stat3.

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“…The yields of -type dimers of (I)±(III) were 97±100% after photoirradiation for 20 h. On the other hand, the yield of the dimer was only 18% for (IV). The CÁ Á ÁC distance between the C C double bonds in (IV) was reported to be 4.109 (4) A Ê (Iwamoto et al, 1989), which is almost the maximum limit for the solid-state reaction. Moreover, the intermolecular NÐ HÁ Á ÁO hydrogen-bond network in (IV) is different from that in (II).…”

Section: Introductionmentioning

confidence: 93%

Crystal-to-crystal photodimerization of trans-cinnamamides

Hosomi

Ito

Ohba

2000

Acta Crystallogr Sect B

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In the crystals of trans-4-methylcinnamamide, C10HT11NO (I), trans-4-chlorocinnamamide, C9H8ClNO (II), trans-3-(2-thienyl)acrylamide, C7H7NOS (III), and trans-cinnamamide, C9H9NO (IV), the shortest intermolecular C...C distances between the C=C double bonds are 3.670 (2), 3.632 (2), 3.762 (3) and 4.120 (2) A, respectively, for the pair of molecules related by a center of symmetry. The structure analysis was also carried out for trans-2-(p-chlorophenyl)-cis4-(p-chlorophenyl)-1-trans-3-diamidocyclobutane, C18H16Cl2N2O2 (V), which is the alpha-type photodimer of (II). The NH...O hydrogen-bond networks in (I)-(III) are composed of two-dimensional pleated sheets, and those in (IV) and (V) of one-dimensional flat ribbons. The single crystals of (I), (II) and (IV) were photoirradiated with a 250 W ultra-high-pressure mercury lamp through a band-pass filter or a long-pass filter for 2-5 h. The photodimer was produced in each crystal with retention of the single-crystal form. The populations of the dimers were converged to 86.2 (4), 48.4 (6) and 4.5 (2)% in the refinement of the crystals after photoirradiation, (I'), (II') and (IV'), respectively. Although the intermolecular N-H...O hydrogen-bond network remained in (I') and (II'), the network was partly broken in (IV') in the process of photoreaction.

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Structure of cinnamamide

Abstract: Abstract. C9H9NO , monoclinic, P21/a, a= 16.015 (3), b=5.072(1), c =9.563(2)A, fl=93.99(2) ° , V= 775.0 (3) A 3, Z =4, Dm=1.26(2), Dx=1.261Mgm -3, CuKa, 2 =1-5418A, p=0.63mm -1, F(000)=312, T= 295 K, R = 0.066 for 1042 reflections with I Fo I >

Cited by 7 publications

References 2 publications

Crystal structure determination as part of an ongoing undergraduate organic laboratory project: 5-[(E)-styryl]-1,3,4-oxathiazol-2-one

Crystal structure determination as part of an ongoing undergraduate organic laboratory project: 5-[(E)-styryl]-1,3,4-oxathiazol-2-one

Potent and Selective Phosphopeptide Mimetic Prodrugs Targeted to the Src Homology 2 (SH2) Domain of Signal Transducer and Activator of Transcription 3

Crystal-to-crystal photodimerization of trans-cinnamamides

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