2591-98-2Relevant academic research and scientific papers
Palladium(II)-catalyzed oxidation of l-tryptophan by hexacyanoferrate(III) in perchloric acid medium: A kinetic and mechanistic approach
Fawzy, Ahmed
, p. 247 - 256 (2016)
The catalytic effect of palladium(II) on the oxidation of l-tryptophan by potassium hexacyanoferrate(III) has been investigated spectrophotometrically in aqueous perchloric acid medium. A first order dependence in [hexacyanoferrate(III)] and fractional-first order dependences in both [l-tryptophan] and [palladium(II)] were obtained. The reaction exhibits fractional-second order kinetics with respect to [H +]. Reaction rate increased with increase in ionic strength and dielectric constant of the medium. The effect of temperature on the reaction rate has also been studied and activation parameters have been evaluated and discussed. Initial addition of the reaction product, hexacyanoferrate(II), does not affect the rate significantly. A plausible mechanistic scheme explaining all the observed kinetic results has been proposed. The final oxidation products are identified as indole-3-acetaldehyde, ammonium ion and carbon dioxide. The rate law associated with the reaction mechanism is derived.
Modulating weak interactions for molecular recognition: A dynamic combinatorial analysis for assessing the contribution of electrostatics to the stability of CH-π bonds in water
Jiménez-Moreno, Ester,G?mez, Ana M.,Bastida, Agatha,Corzana, Francisco,Jiménez-Oses, Gonzalo,Jiménez-Barbero, Jesús,Asensio, Juan Luis
, p. 4344 - 4348 (2015)
Electrostatic and charge-transfer contributions to CH-π complexes can be modulated by attaching electron-withdrawing substituents to the carbon atom. While clearly stabilizing in the gas phase, the outcome of this chemical modification in water is more difficult to predict. Herein we provide a definitive and quantitative answer to this question employing a simple strategy based on dynamic combinatorial chemistry.
11-Step Total Synthesis of Araiosamines
Tian, Maoqun,Yan, Ming,Baran, Phil S.
, p. 14234 - 14237 (2016)
A concise route to a small family of exotic marine alkaloids known as the araiosamines has been developed, and their absolute configuration has been assigned. The dense array of functionality, high polarity, and rich stereochemistry coupled with equilibrating topologies present an unusual challenge for chemical synthesis and an opportunity for innovation. Key steps involve the use of a new reagent for guanidine installation, a remarkably selective C-H functionalization, and a surprisingly simple final step that intersects a presumed biosynthetic intermediate. Synthetic araiosamines were shown to exhibit potency against Gram-positive and -negative bacteria despite a contrary report of no activity.
Flavin-photosensitized production of indole-3-acetaldehyde from tryptophan
Koshiba,Yamauchi,Matsuyama,Miyakado,Sori,Sato
, p. 7603 - 7606 (1993)
Photochemical reaction of tryptophan with flavin was performed under anaerobic condition to give indole-3-acetaldehyde as a major product.
Indolyl-3-acetaldoxime dehydratase from the phytopathogenic fungus Sclerotinia sclerotiorum: Purification, characterization, and substrate specificity
Pedras, M. Soledade C.,Minic, Zoran,Thongbam, Premila D.,Bhaskar, Vangala,Montaut, Sabine
, p. 1952 - 1962 (2010)
The purification and characterization of indolyl-3-acetaldoxime dehydratase produced by the plant fungal pathogen Sclerotinia sclerotiorum is described. The substrate specificity indicates that it is an indolyl-3-acetaldoxime dehydratase (IAD, EC 4.99.1.6), which catalyzes transformation of indolyl-3-acetaldoxime to indolyl-3-acetonitrile. The enzyme showed Michaelis-Menten kinetics and had an apparent molecular mass of 44 kDa. The amino acid sequence of IAD, determined using LC-ESI-MS/MS, identified it as the protein SS1G-01653 from S. sclerotiorum. IADSs was highly homologous (84% amino acid identity) to the hypothetical protein BC1G-14775 from Botryotinia fuckeliana B05.10. In addition, similarity to the phenylacetaldoxime dehydratases from Gibberella zeae (33% amino acid identity) and Bacillus sp. (20% amino acid identity) was noted. The specific activity of IADSs increased about 17-fold upon addition of Na2S2O4 under anaerobic conditions, but in the absence of Na2S2O 4 no significant change was observed, whether aerobic or anaerobic conditions were used. As with other aldoxime dehydratases isolated from microbes, the role of IADSs in fungal plant pathogens is not clear, but given its substrate specificity, it appears unlikely that IADSs is a general xenobiotic detoxifying enzyme.
A Soluble Protein Factor from Chinese Cabbage Converts Indole-3-acetaldoxime to IAA
Helmlinger, Juergen,Rausch, Thomas,Hilgenberg, Willy
, p. 615 - 618 (1987)
A soluble enzyme preparation from Chinese cabbage seedlings (Brassica campestris ssp. pekinensis) which catalyses the conversion of indole-3-acetaldoxime (IAOX) to IAA was partially purified by ion exchange chromatography.After purification enzyme activity was stable for more than 6 hr.Substrate kinetics showed a Km value of 50 μM; the pH optimum was 7.The conversion of IAOX to IAA was increased by NAD, NADP or FAD, but none of them seemed to be a preferential co-substrate.Besides IAA some labelled indole-3-acetaldehyde (IAALD) could be extracted from the reaction mixture.Addition of unlabelled IAALD at 100 nmol/ml led to a significant inhibition of IAA formation while some label accumulated in the aldehyde.Indole-3-acetonitrile was never detected as a reaction product.The results are compared with those from earlier in vivo experiments and are discussed in view of their significance for IAA biosynthesis in the Brassicaceae.Key Word Index - Brassica campestris ssp. pekinensis; Cruciferae; Chinese cabbage; indole-3-acetaldoxime; indole-3-acetaldehyde; IAA biosynthesis.
S -indole benzamide derivative as well as preparation method and application thereof
-
, (2021/09/15)
S - Indole benzamide derivatives as well as a preparation method and application thereof relate to the technical field of pharmacy. The derivative has a structural formula. The specific preparation method comprises the following steps: taking indole as a starting raw material and performing acylation reaction. Reaction, oxidation reaction, (R)- (+) -tert-butylsulfenamide asymmetric synthesis reaction, hydrolysis reaction and acylation reaction to give the target product. By means of the method, a novel antiviral drug with a development prospect can be obtained, and the yield is high.
Towards the Sarpagine-Ajmaline-Macroline Family of Indole Alkaloids: Enantioselective Synthesis of an N-Demethyl Alstolactone Diastereomer
Dagoneau, Dylan,Wang, Qian,Zhu, Jieping
supporting information, p. 4866 - 4873 (2020/04/15)
the strategy involving the use of functionalized tetrahydro-6H-cycloocta[b]indol-6-one is reported as a key intermediate for synthesis of members of the sarpagine-ajmaline-macroline family of monoterpene indole alkaloids. The desired tricycle was synthesized through the following key steps: 1) Evans’ syn-selective aldolization; 2) Liebeskind–Srogl cross-coupling using the phenylthiol ester of 3-chloropropanoic acid as a surrogate of acrylic thioester for the synthesis of 2,3-disubstituted indoles; and 3) ring-closing metathesis (RCM) for the formation of the eight-membered ring. An N-allylation followed by intramolecular 1,4-addition was planned for synthesis of the vobasine class of natural products. However, attempted cyclizations under a diverse set of conditions involving anionic, radical, and organopalladium/organonickel species failed to produce the bridged ring system. On the other hand, esterification of the pendant primary alcohol function with acetoacetic acid, followed by intramolecular Michael addition, afforded the desired tetracycle with excellent diastereoselectivity. Subsequent functional group manipulation and transannular cyclization of the amino alcohol afforded the N(1)-demethyl-3,5-diepi-alstolactone. We believe that the same synthetic route would afford the alstolactone should the amino alcohol with appropriate stereochemistry be used as the starting material.
Stereospecific access to bridged [n.2.1] skeletons through gold-catalyzed tandem reaction of indolyl homopropargyl amides
Tan, Tong-De,Zhu, Xin-Qi,Jia, Mei,Lin, Yongjia,Cheng, Jun,Xia, Yuanzhi,Ye, Long-Wu
supporting information, p. 1309 - 1312 (2019/11/26)
An efficient gold-catalyzed anti-Markovnikov cycloisomerization-initiated tandem reaction of Boc-protected indole tethered homopropargyl amides has been achieved. This method delivers a wide range of valuable bridged aza-[n.2.1] skeletons (n = 3–7) at room temperature with high diastereoselectivity and enantioselectivity by a chirality-transfer strategy. Moreover, the gold-catalyzed tandem reaction of homopropargyl alcohol is also achieved to produce the bridged oxa-[3.2.1] skeleton.
Design, synthesis and evaluation of novel (S)-tryptamine derivatives containing an allyl group and an aryl sulfonamide unit as anticancer agents
Guo, Zhenbo,Xu, Yiming,Peng, Yujie,Haroon ur Rashid,Quan, Wei,Xie, Peng,Wu, Lichuan,Jiang, Jun,Wang, Lisheng,Liu, Xu
, p. 1133 - 1137 (2019/03/06)
A series of (S)-tryptamine derivatives containing an allyl group and an aryl sulfonamide unit were designed, synthesized and evaluated for their potential application as anticancer agents. The structures of the synthesized compounds were characterized by 1H NMR, 13C NMR and ESI-MS spectral analyses. The target compounds were evaluated for their in vitro cytotoxicity against HepG2, HeLa, CNE1 and A549 human cancer cell lines. Some of the synthesized compounds showed moderate to good anticancer activities against four selected cancer cell lines, among of which 6ag was found to be the most active analogue possessing IC50 values 16.5–18.7 μM. Further mechanism studies revealed that compound 6ag could significantly induce HepG2 cell cycle arrest at G1 phase, promote cell apoptosis, and inhibit the colony formation as well.
