38871-41-9|2,3-Dihydrobenzo[b][1,4]dioxine-5-carbonyl chloride| Ambeed

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Quality Control of [ 38871-41-9 ] Purity: 95% SDS Specification

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Product Citations

Novel Psilocin Prodrugs with Altered Pharmacological Properties as Candidate Therapies for Treatment-Resistant Anxiety Disorders

Raithatha, Sheetal A. ; Hagel, Jillian M. ; Matinkhoo, Kaveh ; Yu, Lisa ; Press, David ; Cook, Sarah G. , et al.

DOI: 10.1021/acs.jmedchem.3c01225 PubMed ID: 37983270 JMC,2023, 67(2): 1024-1043.

Abstract: The psychedelic prodrug psilocybin has shown therapeutic benefits for the treatment of numerous psychiatric conditions. Despite pos. clin. end points targeting depression and anxiety, concerns regarding the duration of the psychedelic experience produced by psilocybin, associated with enduring systemic exposure to the active metabolite psilocin, pose a barrier to its therapeutic application. Our objective was to create a novel prodrug of psilocin with similar therapeutic benefits but a reduced duration of psychedelic effects compared with psilocybin. Here, we report the synthesis and functional screening of 28 new chem. entities. Our strategy was to introduce a diversity of cleavable groups at the 4-hydroxy position of the core indole moiety to modulate metabolic processing. We identified several novel prodrugs of psilocin with altered pharmacokinetic profiles and reduced pharmacol. exposure compared with psilocybin. These candidate prodrugs have the potential to maintain the long term benefits of psilocybin therapy while attenuating the duration of psychedelic effects.

Purchased from AmBeed: 77877-94-2 ; 7693-46-1 ; 33657-49-7 ; 38871-41-9 ; 20289-26-3 ; 7693-46-1 ; 2251-50-5 ; 35180-01-9 ; 4090-55-5 ; 54322-65-5 ; 52061-51-5 ; 63881-16-3 ; 5402-53-9

Product Details of [ 38871-41-9 ]

CAS No. :	38871-41-9
Formula :	C₉H₇ClO₃
M.W :	198.60
SMILES Code :	ClC(=O)C1=CC=CC2=C1OCCO2
MDL No. :	MFCD04972616
InChI Key :	IEWVBBWTJOHHCY-UHFFFAOYSA-N
Pubchem ID :	2795031

Safety of [ 38871-41-9 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H314
Precautionary Statements:	P280-P305+P351+P338-P310
Class:	8
UN#:	3261
Packing Group:	Ⅲ

Application In Synthesis of [ 38871-41-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 38871-41-9 ]

[ 38871-41-9 ] Synthesis Path-Downstream 1~35

1
[ 4442-53-9 ]
[ 38871-41-9 ]

Yield	Reaction Conditions	Operation in experiment
		PREPARATION 14: 2,3-ETHYLENEDIOXYBENZOYL CHLORIDE By carrying out the procedure as in Preparation 2--Stage B, but replacing 4,5-methylenedioxy-2-nitrobenzoic acid by 2,3-ethylenedioxybenzoic acid, the title product is obtained.
	With thionyl chloride; at 70 - 80℃; for 4h;	General procedure: The starting two acids (<strong>[4442-53-9]2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid</strong> and 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylic acid) shoud be activated by firstly SOCl2: acid (100 mg) and (6-10 mL) was mixed and stirred at reflux 80 ? for 4 hours. The reaction mixture was cooled and evaporated to give reactive acyl chloride obtained as an oil, which would be dissolved in ethyl acetate (5-6 mL) in the next step.
	With thionyl chloride; In N,N-dimethyl-formamide; for 4h;	General procedure: Method B: SOCl2 (10mL) was added to a stirred solution of compound 3 (20mmol) in anhydrous DMF (50mL). The reaction solution was allowed to stir at room temperature for approximately 4h. Then, active compound 4 (15mmol) and metronidazole (15mmol) were dissolved in CH2Cl2 followed by drop wise addition triethylamine and compound 5 was obtained with yield of 85percent. Compound 5 (10mmol), different substituted benzaldehydes (12mmol) and NaOH (15mmol) were dissolved in DMSO (30mL) at room temperature. The appropriate amount of water was then added in the residue and filtered. The resulting solid was collected and washed with cold water, dried and crystallized from anhydrous ethanol to get the desired compounds. All of the synthetic compounds gave satisfactory analytical and spectroscopic data, which were in full accordance with their depicted structures.

With thionyl chloride; at 85℃; for 1h;

Intermediate 35: 2-diazo-1-(2,3-dihvdro-1 ,4-benzodioxin-5-yl)ethanone; A solution of 1 g of 2,3-dihydro-1 ,4-benzodioxin-5-carboxylic acid (5.55 mmole, Aldrich) in 30.7 mL of SOCI2 was stirred at 850C for 1 h in a dry flask under nitrogen atmosphere. The excess of SOCI2 was removed under reduced pressure, the resulting crude oil was <n="76"/>dissolved in 20.3 ml. of MeCN and to this solution, a solution of TMSCHN2 2M in hexane (11.1 mmole, Aldrich) was added dropwise at O0C. The reaction mixture was warmed to RT and stirred for 2 h. A 1 M solution of citric acid was added and then extracted with AcOEt. The organic layer was washed with a saturated solution of NaHCC>3, dried over Na2SO4 and concentrated under reduced pressure. The crude oil was purified by flash chromatography (from CH to CH/AcOEt 80/20) to give the title compound as a yellow oil (489 mg, 42percent). 1H-NMR (500 MHz, CDCI3): delta 4.29-4.34 (2H, m), 4.35-4.40 (2H, m), 6.25 (1 H, s), 6.92 (1 H, t), 7.02 (1 H, dd), 7.46 (1 H, s); m/z (ES): 205 [M+H]+.

References: [1]Journal of Organic Chemistry,1948,vol. 13,p. 489,493.
[2]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 1609 - 1616.
[3]Patent: US5332735,1994,A .
[4]Journal of Agricultural and Food Chemistry,2011,vol. 59,p. 635 - 644.
[5]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5870 - 5875.
[6]Journal of Medicinal Chemistry,2013,vol. 56,p. 220 - 240.
[7]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2947 - 2954.
[8]Chemistry - A European Journal,2016,vol. 22,p. 12286 - 12289.
[9]Journal of Medicinal Chemistry,2017,vol. 60,p. 180 - 201.
[10]Journal of Medicinal Chemistry,2018,vol. 61,p. 918 - 933.
[11]Patent: WO2008/148853,2008,A1 .Location in patent: Page/Page column 73-74.
[12]Organic Letters,2019,vol. 21,p. 2645 - 2649.

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[ 38871-41-9 ]
[ 139756-02-8 ]
[ 364765-71-9 ]