cas 128-62-1, Narcotine | Articles data

Articles about 128-62-1Total 14 be found

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New reactions of phthalidoisoquinoline alkaloids. Alkoxy exchange reactions and isomerisations of α- and β-narcotine
Substitution of the 7-methoxy group in α- and β-narcotine by other alkoxy groups occurs in an anhydrous ROH/RONa system. It is accompanied by isomerization in position 3 with preference for the α-configuration (5R, 3S). In an alkaline aqueous system (ROH/KOH or 1N KOH only isomerization in position 3 with preference for the β-configuration (5R, 3R) was observed. Some of the new 7-alkoxynarcotines were evaluated for their antitussive activity.
Schmidhammer,Klotzer Kloetzer
p. 664 - 671
(1978)
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Battersby,Spencer
p. 1087,1091
(1965)
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Synthesis and biological evaluation of novel biaryl type α-noscapine congeners
Natural α-noscapine, a known antitussive drug, is also now known to possess weak anticancer efficacy with relatively safe toxicity profile. In this study, we report synthesis and evaluation of novel biaryl type α-noscapine congeners designed by adding aryl unit to the tetrahydroisoquinoline part of natural α-noscapine core. Palladium catalyzed Suzuki cross coupling of 9-bromo α-noscapine with aryl boronic acids was employed using mild and inexpensive reagents to attain desired noscapinoids 5a-g in excellent yields. Screening anti-proliferative activity for new noscapinoids 5b-g, on human cancer cell lines resulted three compounds 5b, 5d and 5f as potent analogues, active against human breast epithelial (MCF-7), human cervix cancer (HeLa) and human lung adenocarcinoma epithelial (A549) cell lines.
Manchukonda, Naresh K.,Naik, Pradeep K.,Sridhar, Balasubramanian,Kantevari, Srinivas
p. 5752 - 5757
(2014)
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An Acid-Catalyzed Epoxide Ring-Opening/Transesterification Cascade Cyclization to Diastereoselective Syntheses of (±)-β-Noscapine and (±)-β-Hydrastine
An acid-catalyzed stereoselective epoxide ring-opening/intramolecular transesterification cascade cyclization reaction and N-Boc deprotection was found to be a successful strategy to construct the phthalide tetrahydroisoquinoline skeleton in one pot. Based on this strategy, the unified and highly diastereoselective routes for the total syntheses of (±)-β-Noscapine and (±)-β-Hydrastine were exploited.
Li, Jihui,Liu, Yongxiang,Song, Xinjing,Wu, Tianxiao,Meng, Jiaxin,Zheng, Yang,Qin, Qiaohua,Zhao, Dongmei,Cheng, Maosheng
p. 7149 - 7153
(2019/09/30)

Synthesis and click reaction of tubulin polymerization inhibitor 9-azido-α-noscapine
Abstract: An efficient protocol for the synthesis of tubulin polymerization inhibitor, 9-azido-α-noscapine 2h from 9-amino-α-noscapine 2g is developed using mild reaction conditions (t-butyl nitrite/trimethylsilyl azide in acetonitrile at room temperature). Operational simplicity, high product yield without formation of any side products are the advantages of this protocol. Further copper catalyzed click reactions of 9-azido-α-noscapine 2h with alkynes 6a–f resulted 9-triazolyl noscapinoids 7a–f resulted in excellent yields. Graphical Abstract: Developed an amicable protocol for the synthesis of 9-azido-α-noscapine from 9-amino-α-noscapineunder mild reaction conditions; was further derivatized to triazoles using click chemistry.[Figure not available: see fulltext.]
Manchukonda, Naresh Kumar,Nagireddy, Praveen Kumar Reddy,Sridhar, Balasubramanian,Kantevari, Srinivas
p. 2457 - 2469
(2017/03/22)

COMPOSITIONS AND METHODS FOR MAKING NOSCAPINE AND SYNTHESIS INTERMEDIATES THEREOF
Methods for the manufacture of the therapeutic chemical compound noscapine and noscapine synthesis intermediates comprising contacting a noscapine pathway precursor selected from a first canadine derivative, a first papaveroxine derivative and narcotine hemiacetal with at least one of the enzymes selected from the group CYP82Y1, CYP82X1, AT1, CYP82X2, OMT, CXE1 and NOS.
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(2015/02/25)

A new total synthesis of (±)-α-noscapine
A new, convergent total synthesis of (±)-α-noscapine was developed on a grams scale through the condensation of 3-trimethylsilyl-meconin derivative 9 and the iodized salt cotarnine derivative 20 as the key step. Staring from simple 2,3-dimethoxybenzoic acid, piperonal and 2,2-dimethoxyethanamine, through the traditional chemical processes to give the final product in 11.6% yield over 14 steps.
Mao, Yongjun,Song, Shuai,Zhao, Dongmei,Cheng, Maosheng
p. 2633 - 2640
(2014/01/06)

Copper(I) mediated facile synthesis of potent tubulin polymerization inhibitor, 9-amino-α-noscapine from natural α-noscapine
Facile synthesis of natural α-noscapine analogue, 9-amino-α-noscapine, a potent inhibitor of tubulin polymerization for cancer therapy, is achieved via copper(I) iodide mediated in situ aromatic azidation and reduction of 9-bromo-α-noscapine (obtained by bromination of natural α-noscapine) with NaN3 in DMSO at 130 °C in the presence of l-proline as an amino acid promoter. The protocol developed here avoided isolation of 9-azido-α-noscapine and did not cleave the sensitive C-C bond between two heterocyclic phthalide and isoquinoline units.
Manchukonda, Naresh K.,Sridhar, Balasubramanian,Naik, Pradeep K.,Joshi, Harish C.,Kantevari, Srinivas
supporting information; experimental part
p. 2983 - 2987
(2012/06/15)

Blocking group-directed diastereoselective total synthesis of (±)-α-noscapine
A new approach for the diastereoselective synthesis of (±)-α- noscapine, a phthalide tetrahydroisoquinoline alkaloid exhibiting several biological activities, is described. The strategy features a blocking group-directed Bischler-Napieralski reaction followed by diastereoselective reduction (α/β>23:1). One of the key intermediates, phthalide-3-carboxylic acid, could be efficiently prepared from simple benzoic acid derivative and glyoxylic acid in one-pot.
Ni, Jizhi,Xiao, Heping,Weng, Lipeng,Wei, Xiaofeng,Xu, Youjun
p. 5162 - 5167
(2011/07/31)

Combination of benzyl-4, 5-dihydro-1H-imidazole derivative and an opioid receptor ligand
The present invention refers to a combination of a Compound A, a benzyl-4,5-dihydro-1 H-imidazole derivative according to formula (I) and a Compound B, an opioid receptor ligand; especially of xylometazoline or oxymetazoline and a μ-opioid receptor agonist, most preferably of xylometazoline or oxymetazoline and morphine; a medicament comprising this combination; a pharmaceutical formulation for nasal application comprising this combination; or the use of this combination for the treatment of the symptoms of pain, or the prevention or the prophylaxis of the symptoms of pain, whereas pain particularily encompasses visceral pain, chronic pain, cancer pain, acute pain or neuropathic pain, specifically involving also breakthrough pain.
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(2009/01/24)

Delivery systems and methods for noscapine and noscapine derivatives, useful as anticancer agents
The present invention relates to methods useful for the treatment of neoplastic diseases, tumor cells, and the treatment of cancer delivering compounds of the formula The invention provides various methods of delivering such compounds, combinations of treatments, and altering such compounds to enhance their effectiveness.
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(2008/06/13)

Noscapine and noscapine derivatives, useful as anticancer agents
Compounds such as formula (I) are useful in the treatment of tumor cells and the treatment of cancer.
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(2008/06/13)

TOTAL SYNTHESIS OF (+/-)-α-NARCOTINE VIA BISCHLER-NAPIERALSKI CYCLIZATION
Refinement of the synthesis of the phthalideisoquinoline alkaloid (+/-)-α-narcotine by Bischler-Napieralski reaction is discussed.The total synthesis of (+/-)-α-narcotine and its "unnatural" regioisomer has been completed.
Varga, Zsofia,Blasko, Gabor,Doernyei, Gabor,Szantay, Csaba
p. 831 - 837
(2007/10/02)

Novel Zinc-Promoted Alkylation of Iminium Salts. New Synthesis of Benzylisoquinoline, Phthalidylisoquinoline, and Protoberberine Alkaloids and Related Compounds
Zinc-promoted reductive coupling reaction of iminium salts with alkyl halides was found to be a successful key reaction for synthesis of a variety of alkaloids such as benzylisoquinoline, phthalidylisoquinoline, and protoberberine alkaloids.More specifically, laudanosine, cordrastine, hydrastine, narcotine, tetrahydropalmatine, and canadine were obtained.A new route for the synthesis of the emetine and yohimbine skeletons was exploited.
Shono, Tatsuya,Hamaguchi, Hiroshi,Sasaki, Manji,Fujita, Shumei,Nagami, Kimihiko
p. 1621 - 1628
(2007/10/02)

Reactions of narcotine isomers with cyanogen bromide
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Kerekes,Gaal Gy.
p. 343 - 353
(2007/10/02)

Chemical Properties

Appearance/Colour :Crystalline solid
Melting Point: 174-176 °C(lit.)
Boiling Point: 565.316 °C at 760 mmHg
Flash Point:295.692 °C
Density: 1.333 g/cm³
Solubility:Practically insoluble in water, soluble in acetone, slightly soluble in ethanol (96 per cent). It dissolves in strong acids; on dilution of the solution with water, the base may be precipitated.
Storage Temp.:-20°C Freezer, Under Inert Atmosphere
Vapor Pressure: 4.83E-14mmHg at 25°C
Refractive Index: 1.5614 (estimate)
PKA: 7.8(at 25℃)
Merck: 13,6752
PSA: 84.48000
LogP: 2.86840

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128-62-1

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Chemical Properties

Appearance/Colour :Crystalline solid

Melting Point: 174-176 °C(lit.)

Boiling Point: 565.316 °C at 760 mmHg

Flash Point:295.692 °C

Density: 1.333 g/cm³

Solubility:Practically insoluble in water, soluble in acetone, slightly soluble in ethanol (96 per cent). It dissolves in strong acids; on dilution of the solution with water, the base may be precipitated.

Storage Temp.:-20°C Freezer, Under Inert Atmosphere

Vapor Pressure: 4.83E-14mmHg at 25°C

Refractive Index: 1.5614 (estimate)

PKA: 7.8(at 25℃)

Merck: 13,6752

PSA: 84.48000

LogP: 2.86840

Article Database

128-62-1

Articles about 128-62-1Total 14 be found

More Articles about upstream products of 128-62-1

More Articles about downstream products of 128-62-1

Chemical Properties

Appearance/Colour :Crystalline solid

Melting Point: 174-176 °C(lit.)

Boiling Point: 565.316 °C at 760 mmHg

Flash Point:295.692 °C

Density: 1.333 g/cm3

Solubility:Practically insoluble in water, soluble in acetone, slightly soluble in ethanol (96 per cent). It dissolves in strong acids; on dilution of the solution with water, the base may be precipitated.

Storage Temp.:-20°C Freezer, Under Inert Atmosphere

Vapor Pressure: 4.83E-14mmHg at 25°C

Refractive Index: 1.5614 (estimate)

PKA: 7.8(at 25℃)

Merck: 13,6752

PSA: 84.48000

LogP: 2.86840

Density: 1.333 g/cm³