Synthesis, characterization and pharmacological profile of tropicamide enantiomers

Dei, Silvia; Bellucci, Cristina; Ghelardini, Carla; Romanelli, Maria Novella; Spampinato, Santi

doi:10.1016/0024-3205(96)00208-1

Cited by 25 publications

(13 citation statements)

References 10 publications

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“…8b ). Furthermore, a creative synthetic route for chiral tropic acid which can be readily converted to tropicamide, hyoscyamine, scopolamine and anisodamine was developed 42 , 44 . As shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Organosilicon compounds are essential synthetic reagents and intermediates in modern organic synthesis, and the Si atom itself is a key element in many functional materials and bioactive molecules. Particularly, chiral β-aldehydesilanes are valuable intermediates, which can be readily converted to other versatile building blocks occurring in a variety of small molecule pharmaceuticals and natural products, such as drugs A (angiotensin-converting enzyme inhibitor), B (HIV protease inhibitor) 38 , fasidotril 39 , candoxatril 40 , venlafaxine 41 , tropicamide 42 , and natural products scopolamine 43 , 44 and anisodamine 45 (Fig. 1c ).…”

Section: Introductionmentioning

confidence: 99%

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Silicon-oriented regio- and enantioselective rhodium-catalyzed hydroformylation

You

Yang

et al. 2018

Nat Commun

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Hydroformylation of 1,2-disubstituted alkenes usually occurs at the α position of the directing heteroatom such as oxygen atom and nitrogen atom. By contrast, to achieve hydroformylation on the β position of the heteroatom is a tough task. Herein, we report the asymmetric rhodium-catalyzed hydroformylation of 1,2-disubstituted alkenylsilanes with excellent regioselectivity at the β position (relative to the silicon heteroatom) and enantioselectivity. In a synthetic sense, we achieve the asymmetric hydroformylation on the β position of the oxygen atom indirectly by using the silicon group as a surrogate for the hydroxyl. Density functional theory (DFT) calculations are carried out to examine energetics of the whole reaction path for Rh/YanPhos-catalyzed asymmetric hydroformylation and understand its regioselectivity and enantioselectivity. Our computational study suggests that the silicon group can activate the substrate and is critical for the regioselectivity.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Silicon-oriented regio- and enantioselective rhodium-catalyzed hydroformylation

You

Yang

et al. 2018

Nat Commun

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“…These receptors reduce the pain threshold when activated [15] whereas they increase it when blocked [48-50, 97]. Conversely, the postsynaptic receptors responsible for the induction of muscarinic analgesia belong to the M 1 subtype.…”

Section: Subtypes Of Muscarinic Receptors Involved In Analgesiamentioning

confidence: 99%

Analgesic and Antineuropathic Drugs Acting Through Central Cholinergic Mechanisms

Bartolini¹,

Mannelli²,

Ghelardini

2011

RPCN

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The role of muscarinic and nicotinic cholinergic receptors in analgesia and neuropathic pain relief is relatively unknown. This review describes how such drugs induce analgesia or alleviate neuropathic pain by acting on the central cholinergic system. Several pharmacological strategies are discussed which increase synthesis and release of acetylcholine (ACh) from cholinergic neurons. The effects of their acute and chronic administration are described. The pharmacological strategies which facilitate the physiological functions of the cholinergic system without altering the normal modulation of cholinergic signals are highlighted. It is proposed that full agonists of muscarinic or nicotinic receptors should be avoided. Their activation is too intense and un-physiological because neuronal signals are distorted when these receptors are constantly activated. Good results can be achieved by using agents that are able to a) increase ACh synthesis, b) partially inhibit cholinesterase activity c) selectively block the autoreceptor or heteroreceptor feedback mechanisms. Activation of M1 subtype muscarinic receptors induces analgesia. Chronic stimulation of nicotinic (N1) receptors has neuronal protective effects. Recent experimental results indicate a relationship between repeated cholinergic stimulation and neurotrophic activation of the glial derived neurotrophic factor (GDNF) family. At least 9 patents covering novel chemicals for cholinergic system modulation and pain control are discussed.

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“…Based on previous studies, these concentrations selectively inhibited each muscarinic receptor subtype studied (Waelbroeck et al, 1990;Lazareno et al, 1993;Shi et al, 1999). However, we cannot completely rule out the possibility that these antagonists may exhibit some cross-reactivity (Dei et al, 1996).…”

Section: Both Natively Expressed M 2 and M 4 Muscarinic Receptors Commentioning

confidence: 99%

Coregulation of Natively Expressed Pertussis Toxin-Sensitive Muscarinic Receptors with G-Protein-Activated Potassium Channels

Clancy¹,

Boyer²,

Slesinger³

2007

Journal of Neuroscience

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Synthesis, characterization and pharmacological profile of tropicamide enantiomers

Cited by 25 publications

References 10 publications

Silicon-oriented regio- and enantioselective rhodium-catalyzed hydroformylation

Silicon-oriented regio- and enantioselective rhodium-catalyzed hydroformylation

Analgesic and Antineuropathic Drugs Acting Through Central Cholinergic Mechanisms

Coregulation of Natively Expressed Pertussis Toxin-Sensitive Muscarinic Receptors with G-Protein-Activated Potassium Channels

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