Prodrugs for Amines

Simplı́cio, Ana Luı́sa; Clancy, John M.; Gilmer, John F.

doi:10.3390/molecules13030519

Cited by 114 publications

(96 citation statements)

References 112 publications

(130 reference statements)

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“…Mp 144.9-146.5 C. R f = 0.64 (ethyl acetate/light petroleum, 1:4). 1 H NMR (400 MHz, 2.11. Synthesis of (9-methoxy-3-thioxo-3H-naphtho[2,1-b]pyran-1-yl) methyl butyrate, 15…”

Section: Synthesis Of (5-methoxymentioning

confidence: 99%

“…R f = 0.71 (ethyl acetate/light petroleum, 1:4). 1 Lawesson's reagent (0.383 g, 9.47 Â 10 À4 mol) was added to a solution of (8-methoxy-3-oxo-3H-naphtho[2,1-b]pyran-1-yl) methyl butyrate (0.103 g, 3.16 Â 10 À4 mol) in toluene (8 mL). The reaction mixture was refluxed for 23 h and followed by TLC (ethyl acetate/light petroleum, 1:4).…”

Section: Synthesis Of (5-methoxymentioning

confidence: 99%

“…Prodrugs, pharmacologically latent derivatives of active agents, can be designed to undergo activation through a specific stimulus. In addition to chemical and/or enzymatic triggers, light is an appealing tool to use for conversion of prodrugs to active agents in a spatially and temporally controlled manner [1][2][3][4][5][6][7][8]. Butyric acid, a saturated unbranched monocarboxylic acid, is one of the shortchain fatty acids.…”

Section: Introductionmentioning

confidence: 99%

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Photoactivable heterocyclic cages in a comparative release study of butyric acid as a model drug

Piloto

Hungerford

Sutter

et al. 2015

Journal of Photochemistry and Photobiology A: Chemistry

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Aiming: at the improvement of the photorelease of butyric acid - a model carboxylic acid drug, a set of heteroaromatic compounds based on acridine, naphtho[2,1-b]pyran, 3H-benzopyran fused julolidine and thioxo-naphtho[2,1-b]pyran were evaluated as benzyl-type phototriggers, in comparison with the well-known o-nitrobenzyl group. The corresponding ester cages were irradiated in a photochemical reactor at 254, 300, 350 and 419 nm, in two solvent systems (methanol or acetonitrile in 80:20 mixtures with HEPES buffer). Photolysis studies showed that, for some of the cages, the release of the active molecule occurred with short irradiation times using 419 nm. Time-resolved fluorescence was used to elucidate their photophysical properties and determine the decay kinetics. Studies were also carried out to assess the suitability of using two-photon excitation to address these compounds, which is advantageous if their use in biological systems is to be considered

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“…Mp 144.9-146.5 C. R f = 0.64 (ethyl acetate/light petroleum, 1:4). 1 H NMR (400 MHz, 2.11. Synthesis of (9-methoxy-3-thioxo-3H-naphtho[2,1-b]pyran-1-yl) methyl butyrate, 15…”

Section: Synthesis Of (5-methoxymentioning

confidence: 99%

Section: Synthesis Of (5-methoxymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Photoactivable heterocyclic cages in a comparative release study of butyric acid as a model drug

Piloto

Hungerford

Sutter

et al. 2015

Journal of Photochemistry and Photobiology A: Chemistry

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“…27 271-272 °C); IR (KBr) n / cm -1 3417, 1658, 1589, 1539, 1500, 1423, 1334, 1292, 1080, 1026, 945, 894, 821, 748, 682, 640 3, 108.7, 113.5, 113.6, 115.1, 116.9, 120.9, 127.3, 139.6, 134.2, 3429, 1654, 1546, 1504, 1427, 1342, 1280, 1018, 960, 775, 721, 1, 121.0, 121.6, 125.6, 125.9, 126.0, 128.6, 134.1, 169.2. N, 3232, 3024, 1666, 1610, 1535, 1462, 1367, 1313, 1111, 1035, 972, 765, 713, 680, 605 7, 125.5, 126.1, 130.6, 169.9.…”

Section: N-(2-hydroxy-5-nitrophenyl)acetamide (3l)mentioning

confidence: 99%

“…For instance, in medicinal chemistry they play a pivotal role affording chemically stable compounds as prodrugs with improved pharmacological profile, and many N-acylated derivatives are in clinical use. 3 On the other hand, acetanilides have natural aptitude to act as ortho directing group in C−H transformations to C−C bond formation, wherein functionalized benzophenone, 4 quinone, 5 bisphenyl, 6 or styrene 7,8 derivatives can be obtained by Pd or Rh catalysis, Figure 1. Besides, the reactivity of some ortho functional group of acetanilides is modulated by the presence of the N-acetyl moiety, which is thus selectively converted to more complex compound, constituting this kind of acetanilide into important synthetic intermediates.…”

Section: Introductionmentioning

confidence: 99%

Eco-Friendly, Catalyst and Solvent-Free, Synthesis of Acetanilides and N-Benzothiazole-2-yl-acetamides

Cunha¹,

Santana²

2016

J. Braz. Chem. Soc.

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An expeditious and green synthesis of acetamides in a solvent-free simple way is described, without catalyst or additives, and in good yield by an instantaneous reaction of anilines or 2-aminothiazoles and acetic anhydride without external heating, and with simple purification. Sixteen substituted acetanilides and four N-benzothiazole-2-yl-acetamides were formed, but aliphatic amines of low molecular weight were not as effective as aromatic ones, and only cyclohexylamine and the enaminone ethyl 3-amino-2-butenoate afforded the corresponding acetamides in good yield.Keywords: acetylation, acetamides, amides, solvente-free reaction, green chemistry IntroductionIn the modern synthetic chemistry the development of greener approaches to the functional group transformations is of continuous interest. 1 There are several ongoing efforts to develop methods which do not need solvent, additives, and without tedious purification. Even reactions carried out without heating and magnetic stirring are relevant contributions, due to the energy economy aspects. 2 The acetamide/acetanilide are functional groups whose importance is beyond of a simple protecting group. For instance, in medicinal chemistry they play a pivotal role affording chemically stable compounds as prodrugs with improved pharmacological profile, and many N-acylated derivatives are in clinical use. 3 On the other hand, acetanilides have natural aptitude to act as ortho directing group in C−H transformations to C−C bond formation, wherein functionalized benzophenone, 4 quinone, 5 bisphenyl, 6 or styrene 7,8 derivatives can be obtained by Pd or Rh catalysis, Figure 1. Besides, the reactivity of some ortho functional group of acetanilides is modulated by the presence of the N-acetyl moiety, which is thus selectively converted to more complex compound, constituting this kind of acetanilide into important synthetic intermediates. 5,[9][10][11][12][13] Due to the abovementioned applications, new developments in the acetylation procedure are still desirables, and representative contributions are described, Figure 2.14-24 Furthermore, in undergraduate courses, the parent acetanilide is extensively synthesized as classical preparation of aromatic amide.25 Therefore, we recently developed a practical solvent-free green synthesis of such compound to experimental courses. 26 However, a search in the literature revealed that when other substituted acetanilides are needed as starting material in the context of a research project, the preparation used is very similar to that of parent acentanilide, which is almost the same of one century ago, which uses large amounts of solvents and additives such as acetic acid and sodium acetate, for instance. [5][6][7][8][9][10][11][12][13][14][15][19][20][21][22][23][24] It should be pointed out that, although there are a few syntheses of acetanilides in the absence of solvent, it is always necessary the use of grinding or microwave heating in these previously described syntheses or, more recurrent, the use of catalyst such as morpholiniu...

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Transition Metal‐Catalyzed CH Functionalizations Using a Transient Directing Group Approach

Das¹,

Aditya²,

Maji³

2022

Handbook of CH-Functionalization

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Transition metal‐catalyzed CH bond functionalization reactions are among the cutting‐edge synthetic tool for step‐economical construction of complex‐molecular architectures. In this realm, the key challenge lies in harnessing the site‐selective activation of the inert CH bonds. Although covalently tethered directing groups rendered reliable results in obtaining positional selectivity, their preinstallation and removal entail multiple steps restricting their applicability. An alternative approach is developed to fill this gap where a transient ligand enables the formation of the directing group in situ and dissociates after the reaction's completion. This strategy is widely known as the transient directing group (TDG) approach. Diverse functionalization such as arylation, alkylation, amination, halogenation, etc., could be achieved using TDG as a powerful means. Moreover, asymmetric functionalization has also been realized utilizing this technique. However, this strategy remained only applicable to aldehydes, ketones, amines, and phenol substrates.

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Prodrugs for Amines

Cited by 114 publications

References 112 publications

Photoactivable heterocyclic cages in a comparative release study of butyric acid as a model drug

Photoactivable heterocyclic cages in a comparative release study of butyric acid as a model drug

Eco-Friendly, Catalyst and Solvent-Free, Synthesis of Acetanilides and N-Benzothiazole-2-yl-acetamides

Transition Metal‐Catalyzed CH Functionalizations Using a Transient Directing Group Approach

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