cas 712-97-0, 6-NITROPIPERONAL | Articles data

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Synthesis, pharmacological evaluation and electrochemical studies of novel 6-nitro-3,4-methylenedioxyphenyl-N-acylhydrazone derivatives: Discovery of LASSBio-881, a new ligand of cannabinoid receptors
We describe herein the discovery of LASSBio-881 (3c) as a novel in vivo antinociceptive, anti-inflammatory, and in vitro antiproliferative and antioxidant compound, with a cannabinoid ligand profile. We observed that LASSBio-881 (3c) was able to bind to CB1 receptors (71% at 100 μM) and also to inhibit T-cell proliferation (66% at 10 μM) probably by binding to CB2 receptors, in a non-proapoptotic manner, different from anandamide (1). It was also demonstrated that LASSBio-881 (3c) had an important antioxidant profile toward free radicals (DPPH and hydroxyl), probably due to its particular redox behavior, which reflects the presence of both nitro and 3,5-di-tert-butyl-4-hydroxyphenyl sub-units, as demonstrated by cyclic voltammetry studies. In addition, we showed that these structural sub-units are essential for the observed pharmacological activity.
Duarte, Carolina D.,Tributino, Jorge L.M.,Lacerda, Daniel I.,Martins, Marina V.,Alexandre-Moreira, Magna S.,Dutra, Fernando,Bechara, Etelvino J.H.,De-Paula, Francine S.,Goulart, Marilia O.F.,Ferreira, Juliano,Calixto, Joao B.,Nunes, Marise P.,Bertho, Alvaro L.,Miranda, Ana Luisa P.,Barreiro, Eliezer J.,Fraga, Carlos A.M.
p. 2421 - 2433
(2007)
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Investigation of Novel Primary and Secondary Pharmacophores and 3-Substitution in the Linking Chain of a Series of Highly Selective and Bitopic Dopamine D3 Receptor Antagonists and Partial Agonists
Dopamine D3 receptors (D3R) play a critical role in neuropsychiatric conditions including substance use disorders (SUD). Recently, we reported a series of N-(3-hydroxy-4-(4-phenylpiperazin-1-yl)butyl)-1H-indole-2-carboxamide analogues as high affinity and selective D3R lead molecules for the treatment of opioid use disorders (OUD). Further optimization led to a series of analogues that replaced the 3-OH with a 3-F in the linker between the primary pharmacophore (PP) and secondary pharmacophore (SP). Among the 3-F-compounds, 9b demonstrated the highest D3R binding affinity (Ki = 0.756 nM) and was 327-fold selective for D3R over D2R. In addition, modification of the PP or SP with a 3,4-(methylenedioxy)phenyl group was also examined. Further, an enantioselective synthesis as well as chiral HPLC methods were developed to give enantiopure R- and S-enantiomers of the four lead compounds. Off-target binding affinities, functional efficacies, and metabolic profiles revealed critical structural components for D3R selectivity as well as drug-like features required for development as pharmacotherapeutics.
Shaik, Anver Basha,Kumar, Vivek,Bonifazi, Alessandro,Guerrero, Adrian M.,Cemaj, Sophie L.,Gadiano, Alexandra,Lam, Jenny,Xi, Zheng-Xiong,Rais, Rana,Slusher, Barbara S.,Newman, Amy Hauck
p. 9061 - 9077
(2019)
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Docking, synthesis and pharmacological activity of novel urea-derivatives designed as p38 MAPK inhibitors
p38 mitogen-activated protein kinase (p38 MAPK) is an important signal transducing enzyme involved in many cellular regulations, including signaling pathways, pain and inflammation. Several p38 MAPK inhibitors have been developed as drug candidates to treatment of autoimmune disorders, such as rheumatoid arthritis. In this paper we reported the docking, synthesis and pharmacological activity of novel urea-derivatives (4a-e) designed as p38 MAPK inhibitors. These derivatives presented good theoretical affinity to the target p38 MAPK, standing out compound 4e (LASSBio-998), which showed a better score value compared to the prototype GK-00687. This compound was able to reduce in vitro TNF-α production and was orally active in a hypernociceptive murine model sensible to p38 MAPK inhibitors. Otherwise, compound 4e presented a dose-dependent analgesic effect in a model of antigen (mBSA)-induced arthritis and anti-inflammatory profile in carrageenan induced paw edema, indicating its potential as a new antiarthritis prototype.
De Oliveira Lopes, Raquel,Romeiro, Nelilma Correia,De Lima, Cleverton Kleiton F.,Louback Da Silva, Leandro,Palhares De Miranda, Ana Luisa,Nascimento, Paulo Gustavo B.D.,Cunha, Fernando Q.,Barreiro, Eliezer J.,Lima, Lidia Moreira
p. 264 - 271
(2012)
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Non-alkylator anti-glioblastoma agents induced cell cycle G2/M arrest and apoptosis: Design, in silico physicochemical and SAR studies of 2-aminoquinoline-3-carboxamides
Malignant gliomas are the most common brain tumors, with generally dismal prognosis, early clinical deterioration and high mortality. Recently, 2-aminoquinoline scaffold derivatives have shown pronounced activity in central nervous system disorders. We herein reported a series of 2-aminoquinoline-3-carboxamides as novel non-alkylator anti-glioblastoma agents. The synthesized compounds showed comparable activity to cisplatin against glioblastoma cell line U87 MG in vitro. Among them, we found that 6a displayed good inhibitory activity against A172 and U118 MG glioblastoma cell lines and induced cell cycle arrest in the G2/M phase and apoptosis in U87 MG by flow cytometry analysis. Additionally, 6a displayed low cytotoxicity to several normal human cell lines. In silico study showed 6a had promising physicochemical properties and was predicted to cross the blood–brain barrier. Moreover, preliminary structure–activity relationships are also investigated, shedding light on further modifications towards more potent agents on this series of compounds. Our results suggest this compound has a promising potential as an anti-glioblastoma agent with a differential effect between tumor and non-malignant cells.
Gu, Xiangyu,Liu, Jianwen,Ni, Xintong,Qi, Yingxue,Qian, Xuhong,Shao, Xusheng,Xu, Xiaoyong,Yuan, Pengtao
supporting information

(2021/09/22)

Synthesis of Azepino[1,2-a]indole-10-amines via [6+1] Annulation of Ynenitriles with Reformatsky Reagent
Lewis acid-catalyzed [6+1] annulation reactions of 2-cyano-1-propargyl- and 2-alkynyl-1-cyanomethyl-indoles with Reformatsky reagent are described. 8-Aryl, 8-alkyl-, 8-hetaryl-, 9-aryl, and 9-alkyl-azepino[1,2-a]indole amines were obtained through a 7-endo-mode cyclization of the β-aminoacrylate intermediates. The antiproliferative activity of the azepino[1,2-a]indoles analogs against the HCT-116 cells were also examined.
Iioka, Ryoya,Yorozu, Kohei,Sakai, Yoko,Kawai, Rika,Hatae, Noriyuki,Takashima, Katsuki,Tanabe, Genzoh,Wasada, Hiroaki,Yoshimatsu, Mitsuhiro
supporting information
p. 1553 - 1558
(2021/02/26)

DOPAMINE D3 RECEPTOR SELECTIVE ANTAGONISTS/PARTIAL AGONISTS AND USES THEREOF
Disclosed herein are novel methods of treating pain in a patient in need thereof by providing to the patient a selective dopamine D3 receptor antagonist/partial agonist which when used with an opioid analgesic, can mitigate the development of opioid dependence, by preventing the need for dose escalation while either maintaining the opioid analgesic effect or providing analgesia with a lower dose of the opioid. In addition, the D3 antagonists/partial agonists described herein may be used to augment the effectiveness of current Medication Assisted Treatment regimens (e.g. methadone or buprenorphine) for the treatment of opioid use disorders.
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(2020/05/07)

Self-assembling nanoparticles of dually hydrophobic prodrugs constructed from camptothecin analogue for cancer therapy
Nanomedicines have shown success in cancer therapy in recent years because of their excellent solubility in aqueous solution and drug accumulation through controlled release in tumor tissues, but the preparation of most nanomedicines still requires ionic materials, surfactants or the amphiphilic structure to maintain nanoparticle stability and function. In this study, we developed a couple of novel dually hydrophobic prodrugs (DHPs) by combining two hydrophobic compounds through different linkers and elaborated their self-assembly mechanisms by virtue of computational simulation. Importantly, without using any excipients, FL-2 NPs exhibited significantly prolonged retention in blood circulation and displayed a remarkable anti-tumor effect at very low concentration in vivo. Both DHPs consisted of camptothecin structural analogue(FL118) and a marine natural product (ES-285). Comparative experiments proved that these compounds could quickly form nanoparticles by way of simple preparation and remained relatively stable for long periods in PBS. FL-2 NPs linked with a disulphide bond could rapidly release bioactive FL118 after being triggered by endogenous reductive stimulus to exert anti-cancer effects. Overall, this study provides a new strategy for design of therapeutic nanomedicines consisting of dually hydrophobic molecules for cancer therapy.
Guan, Huashi,Jiang, Tao,Liu, Jiannan,Liu, Xuemeng,Wang, Xueting,Wu, Guanzhao,Yin, Ruijuan,Yu, Mingming,Yu, Rilei,Zhang, Yixuan
supporting information

(2020/05/25)

Synthesis of new quinoline-piperonal hybrids as potential drugs against Alzheimer’s disease
Six quinoline-piperonal hybrids were synthesized and evaluated as potential drugs against Alzheimer’s disease (AD). Theoretical analysis of the pharmacokinetic and toxicological properties of the compounds suggest that they present good oral bio-availability and are also capable of penetrating the blood–brain barrier, qualifying as leads for new drugs against AD. Evaluation of their inhibitory capacity against acetyl-and butyrilcholinesterases (AChE and BChE) through Ellmann’s test showed that three compounds present promising results with one of them being capable of inhibiting both enzymes. Further docking studies of the six compounds synthesized helped to elucidate the main interactions that may be responsible for the inhibitory activities observed.
Brum, Juliana de Oliveira C.,Neto, Denise Cristian F.,de Almeida, Joyce Sobreiro F. D.,Lima, Josélia Alencar,Kuca, Kamil,Fran?a, Tanos Celmar C.,Figueroa-Villar, José D.
(2019/09/07)

Pyrrolo[2,1-c][1,4] benzodiazepine-3,11-diones protect SHSY-5Y cells from Cd-induced apoptosis involving suppression of endoplasmic reticulum stress
Cadmium (Cd) is a potent toxic heavy metal, some studies showed that Cd-induced apoptosis is through ER stress pathway. Compounds of pyrrolo[2,1–c][1,4]benzodiazepine (PBD)-3,11-diones were discovered as potent neuroprotective agents against Cd-induced toxicity in SH-SY5Y cells for the first time. In this study, twenty-six PBD-3,11-dione derivatives were synthesized and evaluated for their neuroprotective activity against Cd-induced toxicity by CCK-8 assay. Their preliminary SARs studies indicated that various substituents were tolerated on the benzene ring, and alkyl heterocycles groups at the N10-position of the PBD-3,11-dione scaffold were important for the activities. Among them, compound 13c exhibited the best activity (cell viability = 68.6%, 25 μM). Furthermore, we found that the compound 13c could inhibit cadmium-induced cell apoptosis with the downregulation of the ER stress markers GRP78, CHOP, cleaved-caspase12 and cleaved-caspase3 through western blotting. The results of in silico evaluation of ADME/T properties showed that 13c exhibited medium BBB penetration level and promising toxicity profiles. These results proved the potential of 13c as a promising lead compound against Cd-induced neurotoxicity.
Ma, Chao,Du, Ke,Zhao, Ying,Zhang, Linkui,Hu, Baichun,Cheng, Maosheng
p. 5151 - 5158
(2018/09/27)

Novel 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones: Synthesis and antileishmanial effects against Leishmania amazonensis
A series of eleven 3,4-methylenedioxyde-6-X-benzaldehyde-thiosemicarbazones (16-27) was synthesised as part of a study to search for potential new drugs with a leishmanicidal effect. The thiosemicarbazones, ten of which are new compounds, were prepared in good yields (85-98%) by the reaction of 3,4-methylenedioxyde-6-benzaldehydes (6-X-piperonal), previously synthesised for this work by several methodologies, and thiosemicarbazide in ethanol with a few drops of H2SO4. These compounds were evaluated against Leishmania amazonensis promastigotes, and derivatives where X = I (22) and X = CN (23) moieties showed impressive results, having IC50 = 20.74 μM and 16.40 μM, respectively. The intracellular amastigotes assays showed IC50 = 22.00 μM (22) and 17.00 μM (23), and selectivity index >5.7 and >7.4, respectively, with a lower toxicity compared to pentamidine (positive control, SI = 4.5). The results obtained from the preliminary QSAR study indicated the hydrophobicity (log P) as a fundamental parameter for the 2D-QSAR linear model. A molecular docking study demonstrated that both compounds interact with flavin mononucleotide (FMN), important binding site of NO synthase.
De Melos, Jorge Luiz R.,Torres-Santos, Eduardo Caio,Fai?es, Viviane Dos S.,De Nigris Del Cistia, Catarina,Sant'Anna, Carlos Maurício R.,Rodrigues-Santos, Cláudio Eduardo,Echevarria, Aurea
p. 409 - 417
(2015/09/28)

Antitumor activity of FL118, a survivin, Mcl-1, XIAP, and cIAP2 selective inhibitor, is highly dependent on its primary structure and steric configuration
We recently reported the identification and characterization of a novel small chemical molecule designated FL118. FL118 selectively inhibits multiple cancer survival and proliferation-associated antiapoptotic proteins (survivin, Mcl-1, XIAP, cIAP2) and eliminates small and large human tumor xenografts in animal models (Ling et al., PLoS One 2012, 7, e45571). Here, we report a follow-up study on the structure-activity relationship (SAR) of the hydroxyl group in the lactone ring of FL118. We found that the superior antitumor efficacy of FL118 heavily depends on its steric configuration through comparing the antitumor activity of FL118 with FL113 (the racemic mixture of FL118). Consistently, FL118 proved much more effective in inhibiting the expression of survivin, Mcl-1, and cIAP2, both in vitro and in vivo, compared to FL113. Additionally, Tet-on controlled induction of survivin or forced expression of Mcl-1 protects cancer cells from FL118-mediated growth inhibition and cell death. To further explore the SAR, we synthesized seven position 20-esterifiable FL118 and FL113 derivatives. Studies on these seven new compounds revealed that keeping a free hydroxyl group of FL118 is also important for high antitumor efficacy. Together, these studies confirm the superior anticancer activity of FL118 and narrow the window for further SAR studies to generate novel analogues based on FL118 core structure on its other potential chemical positions.
Zhao, Jiuyang,Ling, Xiang,Cao, Shousong,Liu, Xiaojun,Wan, Shengbiao,Jiang, Tao,Li, Fengzhi
p. 457 - 467
(2014/03/21)

Toward new camptothecins. Part 6: Synthesis of crucial ketones and their use in Friedl?nder reaction
In the context of the preparation of camptothecin and luotonin A analogs, the synthesis of some key keto-precursors and their use in Friedl?nder condensation are described. This paper also focuses on the stability of these keto intermediates and emphasizes the major differences between indolizinones and pyrroloquinazolinones series. Noteworthy is also the report of some original structures isolated as by-products of some experiments.
Gavara, Laurent,Boisse, Thomas,Hénichart, Jean-Pierre,Da?ch, Adam,Rigo, Beno?t,Gautret, Philippe
experimental part
p. 7544 - 7561
(2010/12/25)

Synthesis and analgesic profile of conformationally constrained N-acylhydrazone analogues: Discovery of novel N-arylideneamino quinazolin-4(3H)-one compounds derived from natural safrole
In this work we reported the synthesis and evaluation of the analgesic, anti-inflammatory, and platelet anti-aggregating properties of new 3-(arylideneamino)-2-methyl-6,7-methylenedioxy-quinazolin-4(3H)-one derivatives (3a-j), designed as conformationally constrained analogues of analgesic 1,3-benzodioxolyl-N-acylhydrazones (1) previously developed at LASSBio. Target compounds were synthesized in very good yields exploiting abundant Brazilian natural product safrole (2) as starting material. The pharmacological assays lead us to identify compounds LASSBio-1240 (3b) and LASSBio-1272 (3d) as new analgesic prototypes, presenting an antinociceptive profile more potent and effective than dipyrone and indomethacin used, respectively, as standards in AcOH-induced abdominal constrictions assay and in the formalin test. These results confirmed the success in the exploitation of conformation restriction strategy for identification of novel cyclic N-acylhydrazone analogues with optimized analgesic profile.
Maia, Rodolfo C.,Silva, Leandro L.,Mazzeu, Eduardo F.,Fumian, Milla M.,de Rezende, Claudia M.,Doriguetto, Antonio C.,Correa, Rodrigo S.,Miranda, Ana Luisa P.,Barreiro, Eliezer J.,Fraga, Carlos Alberto Manssour
experimental part
p. 6517 - 6525
(2009/12/06)

Novel 1,3,4-thiadiazolium-2-phenylamine chlorides derived from natural piperine as trypanocidal agents: Chemical and biological studies
We herein describe the synthesis and characterization of nine new 1,3,4-thiadiazolium-2-phenylamine chlorides derived from natural piperine. We evaluate their toxic effects against the different evolutive forms of Trypanosoma cruzi, and the host cell (murine macrophages). The results obtained show that mesoionic hydrochloride MI possesses the best activity profile. Compound MI may be a prototype for use in the development of a new chemotherapeutic agent with high efficiency, which may be employed in the treatment of Chagas' disease.
da Silva Ferreira, Welisson,Freire-de-Lima, Leonardo,Saraiva, Victor Barbosa,Alisson-Silva, Frederico,Mendonca-Previato, Lucia,Previato, Jose Osvaldo,Echevarria, Aurea,de Lima, Marco Edilson Freire
p. 2984 - 2991
(2008/09/19)

ANTI-INFLAMMATORY AND ANALGESIC PHARMACEUTICAL COMPOSITION CONTAINING SAFROLE N-ACYLHYDRAZONE DERIVATIVES, USE, AND METHOD OF PREPARATION
New derivatives of the 6-nitro-N'-arylmethylidene-1,3-benzodioxol-5-carbohydrazide nucleus are described, having anti-inflammatory and analgesic properties, acting on the central nervous system, and are therefore useful in the treatment of acute and chronic inflammatory diseases and central hyperalgesia in mammals; pharmaceutical compositions containing said compounds and methods of preparation thereof are also described.
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Page/Page column 12

(2008/06/13)

UREIDIC COMPOUNDS, PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AND THEIR USE ON THE TREATMENT OF INFLAMMATORY DISEASES
The present invention describes functionalizeds derivatives of ethyl 6-N- alkyl and/or 6-N-aryl ureas [1 ,3]dioxolo[5,4-g]quinolin-7-carboxylate (3a-z, 4a-z) and similar types (5a-z), of general formula (I, II, III and IV), useful in the treatment and/or prevention of inflammatory diseases, such as acute or chronic inflammatory conditions, different types of arthritis, asthma, Crohn's Disease and diabetes mellitus Type I, among others. These derivatives have the ability of modulate the inflammatory process, acting in mitogen activated protein kinase p-38 (MAPK-p38). Moreover, the derivatives of the present invention present expressive anti-inflammatory properties evaluated in in vivo models. The present invention also discloses processes for the production of such derivatives and harmaceutical com ositions containin the same.
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Page/Page column 13

(2008/06/13)

Synthesis and structure-activity relationships of vasicine analogues as bronchodilatory agents
The series of vasicine (1) analogues, an alkaloid from Adhatoda vasica Nees., were synthesized with changes in A, B or C rings. Compounds 3-19 were evaluated for in vitro bronchodilatory activity using isolated guinea pig tracheal chain. Compounds 3-8 were also synthesized in good yields using microwave-mediated synthesis under solvent free conditions. Compounds 5 and 8 with seven-member C ring were more active than etofylline and caused 100% relaxation of both the histamine and acetylcholine pre-contracted guinea pig tracheal chain. The structure-activity relationship studies showed that the quinazoline and oxo functionalities were essential for activity. The compounds without C ring and instead having aliphatic and phenyl substitutions in B ring showed relaxation against histamine pre-contracted tracheal chain only, 2-methyl substituted analogues, 12 and 13, being most active with 100% relaxation effect. Birkhaeuser Boston 2006.
Mahindroo, Neeraj,Ahmed, Zabeer,Bhagat, Asha,Bedi, Kasturi Lal,Khajuria, Ravi Kant,Kapoor, Vijay Kumar,Dhar, Kanaya Lal
p. 347 - 368
(2007/10/03)

SRN1 reactions in the nitrobenzo[1,3]dioxole series
5-Chloromethyl-6-nitrobenzo[1,3]dioxole has been shown to react with 2-nitropropane anion to give C-alkylation by an SRN1 mechanism. The reaction was extended to various aliphatic, cyclic, and heterocyclic nitronate anions, leading to a new series of nitrobenzo[1,3]dioxole derivatives.
Meuche-Albeny,Rathelot,Crozet,Vanelle
p. 989 - 997
(2007/10/03)

THE ESR SPECTRA, STRUCTURE, AND REACTIVITY OF AROMATIC RADICAL-CATIONS IN SUPERACIDS
The oxidation of aromatic compounds by lead dioxide in superacids based on fluorosulfonic acid at -75 deg C takes place by a one-electron mechanism and leads in many cases to relatively stable radical-cations.The ESR spectra, the isotropic hyperfine coupling constants, data on the reactivity of the radical-cations, and the structures of the final products from their transformations under "long-life" conditions are presented.
Rudenko, A. P.
p. 1946 - 1980
(2007/10/03)

Synthesis of 3-[β-(3,4-dialkyloxyphenyl)ethyl]-4(3H)-oxoquinazolines
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Joshi,Chaudhari,Mogera
p. 431 - 434
(2007/10/02)

SYNTHESIS OF 5,6-DIHYDROXYINDOLE: A NOVEL REDUCTIVE CYCLIZATION OF (E)-4,5-DIHYDROXY-2,β-DINITROSTYRENE
A unique catalytic reductive cyclization of (E)-4,5-dihydroxy-2,β-dinitrostyrene (1) to 5,6-dihydroxyindole (2) is reported.Compound 1 is obtained either by one-step CF3CO2H deprotection of 4,5-dibenzyloxy-2,β-dinitristyrene (7), or by an improved two-step demethylenation of 6-nitropiperonal (5), followed by condensation with CH3NO2.
Murphy, Bryan P.,Banks, Harold D.
p. 321 - 330
(2007/10/02)

Efficient Synthesis of 5,6-Diacetoxyindole: A Stable Eumelanin Precursor
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Murphy, Bryan P.
p. 5873 - 5875
(2007/10/02)

ELECTROCHEMICAL OXIDATION OF ORGANIC COMPOUNDS IN FLUOROSULFONIC ACID. IX. VOLTAMMETRIC CHARACTERISTICS OF THE OXIDATION OF SUBSTITUTED PHENOLS, THEIR DERIVATIVES, AND HETEROCYCLIC COMPOUNDS IN FLUOROSULFONIC ACID AND ACETONITRILE
The electrochemical oxidation of phenols and their alkyl ethers not containing strong electron-withdrawing substituents in fluorosulfonic acid takes place in the form of the benzenonium ions and is irreversible in character.With the introduction of substituents of the -M type into the benzene ring the oxidation process affects the unprotonated molecules to a first approximation and in many cases goes reversibly to the radical-cations.Comparison of the oxidation potentials of the substrates in acetonitrile and fluorosulfonic acid made it possible to reveal certain characteristics of the fine structure of these radical-cations, which is determined by the ability of the latter to interact with the medium.Heterocyclic cations whose oxidation potentials in acetonitrile lie beyond the limit of the discharge of the supporting electrolyte can be oxidized in fluorosulfonic acid.Cations of the quinolinium, isoquinolinium, acridinium, acridizinium, imidazolium, and other series, which have irreversible many-electron waves in acetonitrile, give well-defined reversible peaks for oxidation to the corresponding radical-dications in fluorosulfonic acid.In phenyl- and benzyl-substituted cations the substituents and not the positively charged heterocycle itself can undergo oxidation.
Rudenko, A. P.,Zarubin, M. Ya.,Pragst, F.
p. 2145 - 2165
(2007/10/02)

8,9-Methylenedioxy-3,4-dihydro-1,4,5-benzotriazocin-2(1H)-ones
The title compounds are obtained directly on reaction of 6-chloroacetamidopiperonal with substituted phenylhydrazines.Piperonal was used as starting material. - Keywords: 1,4,5-Benzotriazocines; 6-Aminopiperonal; 6-Chloroacetamidopiperonal; 8,9-Methylenedioxy-1,4,5-benzotriazocines
Lin, Whei Oh,Coutinho, Edson de Souza
p. 1231 - 1236
(2007/10/02)

Mutagen Formation in the Nitrite-Piperic Acid Reaction
The formation of mutagen in the reaction of nitrite with food components analogous to sorbic acid has been extensively investigated, using the microbial mutagenicity tests.Strong mutagenic activity was detected, especially in a nitrite-treated piperine solution, by the rec-assay and the Ames test.Because the same mutagenicity profile was observed in a piperic acid-nitrite reaction mixture, a large scale reaction of sodium nitrite with piperic acid was carried out and four mutagenic reaction products were isolated.One of the main mutagens was identified as 6-nitropiperonal and a formation pathway from nitrite-treated piperine is proposed.
Osawa, Toshihiko,Namiki, Mitsuo,Namiki, Kazuko
p. 3105 - 3108
(2007/10/02)