• 한국염색가공학회지
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• 제9권1호
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• pp.44-49
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• 1997

Recent investigation and developments of A. Iqbal on diketo-pyrrolo-pyrrole (DPP) pigments has prompted us to synthesize and close observation of a few properties of these molecules. Described are synthesis, via 1-phenyl-2-ethoxycarbonyl-5-pyrrolinone intermediate, of asymmetric derivatives such as 1,4-Diketo-3-(4-chlorophenyl)-6-phenyl-pyrrolo-(3,4c)-pyrrole (4), 1,4-Diketo-3-(4-bromophenyl)-6-phenybpyrrolo-(3,4c)-pyrrole (5), 1,4-Diketo-3-(3-cyanophenyl)-6-phenyl-pyrrolo-(3,4c)-pyrrole (6), 1,4-Diketo-3-(4-cyanophenyl)-6-phenyl-pyrrolo-(3,4c)-pyrrole (7), 1,4-Diketo-3-(4-pyridyl)-6-phenyt-pyrrolo-(3,4c)-pyrrole (8), 1,4-Diketo-3-(3-pyridyl)-6-phenyl-pyrrolo-(3,4c)-pyrrole (9), 1,4-Diketo-3-(2-pyridyl)-6-phenyl-pyrrolo-(3,4c)-pyrrole (10), 1,4-Diketo-3-($\beta$-naphthyl)-6-phenyl-pyrrolo-(3,4c)-pyrrole (11), and UV-Vis absorption spectrum of the above compounds. Results from calculation of their absorption maxima using PISYSTEM are also described.

• Bulletin of the Korean Chemical Society
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• 제17권1호
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• pp.61-65
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• 1996

The semiempirical time-dependent Hartree-Fock PM3 calculations have been performed on three polyene systems. In order to study the nonlinear optical properties, we calculated the frequency-dependent first-, second-, and third-order polarizabilities of thiophene-, furan-, pyrrole-nitro polyene systems. The PM3 predicted average and longitudinal polarizabilties increase in the order: thiophene- > pyrrole- > furan-nitro polyene systems. The PM3 predicted limiting average second-order polarizabilities show the order: pyrrole- > furan- > thiophene-nitro polyene systems. The average and longitudinal third-order polarizabilties have the following order: pyrrole- > thiophene- > furan-nitro polyene systems. In these trends, we sugest that pyrrole group is the best donor group among the three polyene systems.

• 약학회지
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• 제39권2호
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• pp.205-209
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• 1995

Methylene protons of benzyl and ethyl ester in ethyl 1-benzyl-2, 3-dioxo-cyclopenta[b]-pyrrole-3a-carboxylate (A) exhibited opposite$^{1}$H-NMR spectral patterns mutually between magnetic equivalence and nonequivalence depending on concentration and temperature. The diastereotopic spectral data of compound A were reported with brief interpretation.

• Bulletin of the Korean Chemical Society
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• 제34권1호
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• pp.313-316
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• 2013

• Archives of Pharmacal Research
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• 제24권5호
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• pp.455-465
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• 2001

The highly potent cytotoxic DNA-DNA cross-linker consists of two cyclopropa[c]pyrrolo[3,4-3]indol-4(5H)-ones insoles [(+)-CPI-I] joined by a bisamido pyrrole (abbreviated to "Pyrrole"). The Pyrrole is a synthetic analog of Bizelesin, which is currently in phase II clinical trials due to its excellent in vivo antitumor activity. The Pyrrole has 10 times more potent cytotoxicity than Bizelesin and mostly form DNA-DNA interstrand cross-links through the N3 of adenines spaced 7 bp apart. The Pyrrole requires a centrally positioned GC base pair for high cross-linking reactivity (i.e., $5^1$-T$AT_2$A*-$3^1$), while Bizelesin prefers purely AT-rich sequences (i.e., $5^1$-T$AT_4$A*-$3^1$, where /(equation omitted) represents the cross-strand adenine alkylation and A* represents an adenine alkylation) (Park et al., 1996). In this study, the high-field $^1$H-NMR and rMD studies are conducted on the 1 1-mer DNA duplex adduct of the Pyrrole where the 5′(equation omitted)TAGTTA*-3′sequence is cross-linked by the drug. A severe structural perturbation is observed in the intervening sequences of cross-linking site, while a normal B-DNA structure is maintained in the region next to the drug-modified adenines. Based upon these observations, we propose that the interplay between the bisamido pyrrole unit of the drug and central C/C base pair (hydrogen-bonding interactions) is involved in the process of cross-linking reaction, and sequence specificity is the outcome of those interactions. This study suggests a mechanism for the sequence specific cross-linking reaction of the Pyrrole, and provides a further insight to develop new DNA sequence selective and distortive cross-linking agents.

• Bulletin of the Korean Chemical Society
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• 제19권3호
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• pp.299-307
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• 1998

PM3 semiempirical calculations were carried out to study the frequency-dependent nonlinear optical properties of thiophene, furan, pyrrole, (1,2,4)-triazole, (1,3,4)-oxadiazole, and (1,3,4)-thiadiazole monomers and oligomers. The longitudinal component, αxx, is the largest of three principle components. On the other hand, the out-of-plane component, αzz, is the smallest. Moreover, the out-of-plane component (αzz) of thiophene, furan, pyrrole, (1,2,4)-triazole, (1,3,4)-oxadiazole, and (1,3,4)-thiadiazole monomers show constant changes with increasing optical frequencies. The frequency-dependent first- order polarizabilities increase in the order: thiophene > (1,2,4)-triazole > pyrrole > furan > (1,3,4)-thiadiazole > (1,3,4)-oxa-diazole monomers and oligomers. The effects of β(-2ω;ω,ω) (SHG) shows a larger dispersion compared with (-ω;ω,0) (EOPE) and β(0;-ω,ω) (OR). The second- order polarizabilities of thiophene, furan, pyrrole, (1,2,4)-triazole, (1,3,4)-thiadiazole, and (1,3,4)-oxadiazole monomers for the various second- order effects have the order: β(-2ω;ω,ω) (SHG) > β(-ω;ω,0) (EOPE) > β(0;-ω,ω) (OR) and thiophene > pyrrole > (1,2,4)-triazole > furan > 1,3,4-thiadiazole > 1,3,4-oxadiazole monomers. The third- order polarizabilities for the various third- order effects have the following order: γ(-3ω;ω',ω,ω) (THG) > γ(-2ω;0,ω,ω) (EFISHG) > γ(-ω;ω',-ω,ω) (IDRI) > γ(-ω;0,0,ω) (OKE). The effects of THG increase rapidly with increasing optical frequencies compared with the other effects. In particular, OKE effects increase most slowly with increasing optical frequencies. Also, the effects of THG for thiophene, furan, pyrrole, (1,2,4)-triazole, (1,3,4)-thiadiazole, and (1,3,4)-oxadiazole oligomers show the order thiophene > (1,2,4)-triazole > furan > pyrrole > (1,3,4)-thiadiazole > (1,3,4)-oxadiazole oligomers. In particular, the third- order polarizabilities of thiophene and (1,3,4)-thiadiazole oligomers are about four and three times larger than those of (1,3,4)-oxadiazole and (1,2,4)-triazole oligomer, respectively.

• Natural Product Sciences
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• 제17권3호
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• pp.181-182
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• 2011

Phytochemical investigation of Lycium chinense fruits led to isolation of a new pyrrole compound. The structure of this compound was confirmed as a 5-methoxymethyl-lH-pyrrole-2-carbaaldehyde, a new natural product, by interpretation of 1D ($^1H$, $^{13}C$) and 2D (HMQC, HMBC) spectroscopic data along with HRMS and IR spectroscopic data.

• 대한화학회지
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• 제21권1호
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• pp.32-37
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• 1977

EHT 분자궤도함수법 계산으로 9가지 furan, thiophene 및 pyrrole의 2-치환체의 우세한 형태를 구명하였다. 계산 결과는 furan 유도체의 우세한 형태는 trans형인데 이것은 주로 정전기적 상호작용에 의하여 안정화되어 있으며 thiophene에서는 hetero 고리의 S원자와 카르보닐 산소와의 전자적 콘쥬게이션이, 그리고 pyrrole에서는 정전기적 및 콘쥬게이션 효과가 안정한 형태를 결정하는데 작용하고 있다. EHT계산 결과는 실험결과와도 잘 일치된다.

• Bulletin of the Korean Chemical Society
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• 제9권4호
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• pp.248-251
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• 1988

Mechanism of electrochemical polymerization of pyrrole (Py) on a Pt electrode in acidic aqueous solutions was studied by means of potentiostatic measurements, cyclic voltammetry and chronopotentiometry. Pyrrole molecule appeared to be initially oxidized via two-electron transfer step to produce oxidized pyrrole ion ($Py^+$), which was coupled with a non-oxidized pyrrole to yield a dimerized species, Py-Py. The Py-Py thus formed was further oxidized again via two-electron transfer step, which was followed by coupling with non-oxidized monomer and by concomitant expulsion of a $H^+$. Then the latter chain extension process was repeated. The chain extension and polypyrrole oxidation reactions occurred competitively.

• Bulletin of the Korean Chemical Society
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• 제30권2호
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• pp.423-428
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• 2009

The comparative study of three calix[4]heterocycles (calix[4]pyrrole, calix[4]furan, and calix[4]thiophene) has been theoretically performed by using high-level density functional theory (DFT) at the MPWB1K/6-311G$^{**}$//B3LYP/6- 311G$^{**}$ level. The effect of different hetero-atoms (nitrogen, oxygen, and sulfur) placed in the heterocycles on the conformational flexibility, thermodynamic stability order, cavity sizes, charge distributions, and binding propensities are examined. The thermodynamic stability differences between the conformers are found to be much greater in calix[4]pyrrole compared to those in calix[4]furan and calix[4]thiophene. Relatively larger NH group and higher dipole of a pyrrole ring in calix[4]pyrrole contribute to the higher energy barrier for the conformational conversions and relatively rigid potential energy surface compared to the case of calix[4]furan and calix[4]thiophene. The computational results herein provide theoretical understanding of the conformational flexibility and the thermodynamic nature which can be applied to understand the complexation behavior of the three calix[4]heterocycles.