Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA

Rosa, Flávia A. F. da; Rebelo, Ricardo Andrade; Nascimento, Maria G.

doi:10.1590/s0103-50532003000100003

Cited by 21 publications

(15 citation statements)

References 14 publications

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“…Synthesis Nitrosafrol (2) obtained under standard conditions [7][8][9][10] (HNO 3 / H 2 SO 4 /HAc) afforded the nitro compound 2 and aldehyde 3 with 75.0% and 5.2% yields respectively (scheme 1). Oxidative hydroboration of the side chain of nitrosafrol led to an alcohol at C-3'.…”

Section: Resultsmentioning

confidence: 99%

“…Safrole (1) and its synthetic derivatives (2)(3)(4)(5)(6)(7)(8) were tested in vitro for antiproliferative effect on two human tumor breast cancer cell lines (MDA-MB-231, MCF-7), one human colorectal cancer cell line (DLD-1) and one dermal human fibroblast cell line (DHF). The in vitro growth inhibition assay used was based on sulphorhodamine dye, widely used to quantify cell viability.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Nine Safrole Derivatives and Their Antiproliferative Activity Towards Human Cancer Cells

Espinoza

Madrid

Liber

et al. 2010

J. Chil. Chem. Soc.

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Safrole from sassafras oil (Ocotea pretiosa Mez., Lauraceae), is an abundant natural product showing interesting functionality and chemical structure. Starting from safrole, nine derivatives were prepared and assessed for antiproliferative effect using different human cell lines. The in vitro growth inhibition assay was based on the sulphorhodamine dye to quantify cell viability. Some safrole derivatives, (2E)-3-(3',4'-methylenedioxi)phenyl acrylaldehyde (3) and 4-allyl-5-nitrobenzene-1,2-diol (4) presented better antiproliferative effect than the parent compound on two breast cancer cell lines (MCF-7 and MDA-MB-231) and one human colorectal cancer cell line (DLD-1) with IC 50 values of 55.0 + 7.11 µM, 37.5 + 2.65 µM and 44.0 + 6.92 µM, respectively, without toxicity towards dermal human fibroblast (DHF cells).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of Nine Safrole Derivatives and Their Antiproliferative Activity Towards Human Cancer Cells

Espinoza

Madrid

Liber

et al. 2010

J. Chil. Chem. Soc.

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“…The required azidocinnamic esters are readily formed by condensation of azidoacetic esters and aryl aldehydes (Scheme ). This reaction, named after Isomura, Hemetsberger, and Rees,321–323 is one of the most important indole syntheses324, 325 and was used with success in a number of natural products syntheses such as murrayquinone,326 discorhabdin C, makaluvamine D,327 and varioline ( 45 )65 (Scheme ). Furthermore, this reaction is used in the synthesis of phosphodiesterase inhibitors PDE‐1 ( 328 ) and PDE‐2 ( 327 ), which are related to the antibiotic CC‐1065 (Scheme ) 328.…”

Section: Reactions Of Organic Azidesmentioning

confidence: 99%

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

et al. 2005

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Since the discovery of organic azides by Peter Griess more than 140 years ago, numerous syntheses of these energy-rich molecules have been developed. In more recent times in particular, completely new perspectives have been developed for their use in peptide chemistry, combinatorial chemistry, and heterocyclic synthesis. Organic azides have assumed an important position at the interface between chemistry, biology, medicine, and materials science. In this Review, the fundamental characteristics of azide chemistry and current developments are presented. The focus will be placed on cycloadditions (Huisgen reaction), aza ylide chemistry, and the synthesis of heterocycles. Further reactions such as the aza-Wittig reaction, the Sundberg rearrangement, the Staudinger ligation, the Boyer and Boyer-Aubé rearrangements, the Curtius rearrangement, the Schmidt rearrangement, and the Hemetsberger rearrangement bear witness to the versatility of modern azide chemistry.

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“…Commercially available starting material 5 [9,10] could be prepared from heliotropin. [11,12] The reductions of compound 5 to amine 4b came across some troubles. Reduction reagents such as LiAlH 4 only led to complex results.…”

Section: Resultsmentioning

confidence: 99%

First Total Synthesis of the Proposed Structures of Orisuaveolines A and B

Zhang

et al. 2013

Chin. J. Chem.

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First total synthesis of the proposed structures of β-indoloquinazoline alkaloids orisuaveolines A and B is reported. The key steps of the synthesis included a Pictet-Spengler reaction to build a six-member lactam which further transformed into target molecular by a one-pot condensation. This synthesis provided an access to the proposed structures of orisuaveolines A and B in a short and convenient manner from inexpensive, commercially available starting materials. The structures of our synthesized products were confirmed by 2D-NMR experiments.

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Synthesis of new indolecarboxylic acids related to the plant hormone indoleacetic acid IAA

Cited by 21 publications

References 14 publications

Synthesis of Nine Safrole Derivatives and Their Antiproliferative Activity Towards Human Cancer Cells

Synthesis of Nine Safrole Derivatives and Their Antiproliferative Activity Towards Human Cancer Cells

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

First Total Synthesis of the Proposed Structures of Orisuaveolines A and B

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