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updated December 01, 2022

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Accession Number:
	2016-37083
Author:
	Takanashi N, Suzuki K, Kitajima M, Takayama H
Title:
	Total synthesis of conolidine and apparicine.
Source:
	Tetrahedron Lett. (57, No. 3, 375-8, 2016)
Corporate Information:
	Univ.Chiba
    	Chiba, Japan
Corporate Affiliates:
	Univ.Chiba
Location of Corporation:
	Chiba, Japan
Abstract:
	Total synthesis of indole alkaloids, (+/-)-conolidine (1) and (+/-)-apparicine (2) in 10 and 12 steps respectively 
    	from (E)-3-ethylidene 1-(2-nitrophenylsulfonyl) piperidine 4-carbaldehyde (5) and 2-lithio benzenesulfonyl 
    	indole (4) are reported. Coupling of (5) with (4) in THF at -78 deg, followed by oxidation of the resulting 
    	secondary alcohol with Dess-Martin periodinane gave (S,E)-(3-ethylidene 1-(2-nitrophenylsulfonyl) 
   	piperidin-4-yl) (1-(phenylsulfonyl) 1H-indol 2-yl)methanone (15). Reaction of (15) with KOH in methanol at 
    	reflux temperature, followed by deprotection of 2-nitrophenylsulfonyl (Ns) group with PhSH in one pot afforded 
    	Micalizio's intermediate (3). Reaction of (3) with paraformaldehyde and (+)-CSA gave (1) in 59% yield. 
    	1,2-Addition reaction of (1) with methyl lithium followed by subsequent dehydration with trifluoroacetic acid 
    	gave (2) in 52% yield from (1).
   

   	43 Refs.
Reprint Address:
	Chiba Univ, Grad Sch Pharmaceut Sci, 1-8-1 Inohana, Chiba, Japan, 2608675. (Takayama H, e-mail: 
    	[email protected]).
Common Terms:
	TOTAL/FT, SYNTH./FT, RACEMIC/FT
Linked Terms:
	1: CONOLIDINE/OC, NEW/FT, ANALGESICS/FT, OC/FT
	2: PERICALLINE/OC, NARCOTICS/FT, OC/FT
Derwent Registry Name:
	DR4004436, PERICALLI
Thematic Groups:
	Chemistry
Profile Sections:
	Analgesics (post 1985), Medicinal Chemistry, New Drugs
Subject Headings:
	TOTAL/ft[Further Terms]
	SYNTH./ft[Further Terms]
	RACEMIC/ft[Further Terms]
	CONOLIDINE/oc[Other Context]
	NEW/ft[Further Terms]
	ANALGESICS/ft[Further Terms]
	OC/ft[Further Terms]
	PERICALLINE/oc[Other Context]
	NARCOTICS/ft[Further Terms]
ISSN:
	0040-4039
Language:
	English
CODEN:
	TELEAY
Date Delivered:
	20161125
Year:
	2016
Update Code:
	201648

Accession Number:
	2000-35108
Author:
	Gervelas C, Avramoglou T, Crepin M, Chaubet F, Jozefonvicz J
Conference Information:
	20th Forum on Cancer Study, Paris, France, 2000
Title:
	The effect of sodium phenylacetate and dextran derivatives on the tumor cell line 1205LU. (Fr.).
Original Title:
	Effet du phenylacetate de sodium et de derives du dextrane sur la lignee cellulaire tumorale 1205LU.
Source:
	Bull.Cancer (87, No. 5, 413-14, 2000)
Corporate Information:
	Univ.Paris
    	Villetaneuse; Bobigny, Fr.
Corporate Affiliates:
	Univ.Paris
Location of Corporation:
	Villetaneuse; Bobigny, Fr.
Abstract:
	This study showed that high doses of sodium phenylacetate (SP) and substituted dextran derivatives had antiproliferative
    	effects in 1205 LU human melanoma tumor cells in-vitro. At concentrations achieved in-vivo, SP had no antiproliferative
        effects. Semisynthetic dextrans with methylcarboxylate (MC) and benzylamide (B) substituent (DMCB-type dextrans) had
        antiproliferative effects and inhibited cell adhesion. An in-vivo study with the most active derivative is under way to study 
        the effects of these agents on tumor growth and angiogenesis.


    	In human 1205LU tumor melanoma cells, which form nodules in-vitro that resemble the chemorefractory tumors observed in the 
        lungs of athymic mice, high doses of SP (12-18 mM) exhibited a dose-dependent antiproliferative effect. No 
        antiproliferative effects were achieved at physiological concentrations of SP (1 mM or less). The DMCB-type dextran 
        derivatives had an antiproliferative effect of about 20% at concentrations above 100 ug/ml. Studies with matrigel suggested 
        these DMCB derivatives also inhibited cell adhesion.
Reprint Address:
	LRM, CNRS UMR 7540, Institut Galilee, Universite Paris 13, avenue J.-B.-Clement, 93430 Villetaneuse, France.
Linked Terms:
	1: PHENYLACETATE/PH, SODIUM/PH, TUMOR-CELL/FT, IN-VITRO/FT, SODIUM-SALT/FT, CYTOSTATIC/FT, DOSAGE/FT, 
    	HIGH/FT, ADHESION/FT, DER./FT, MELANOMA/FT, 1205LU-CELL/FT, TISSUE-CULTURE/FT, PH/FT
Derwent Registry Name:
	PHENYLACE
Thematic Groups:
	Pharmacology
Profile Sections:
	Chemotherapy - non-clinical
Subject Headings:
	PHENYLACETATE/ph[Pharmacology]
	SODIUM/ph[Pharmacology]
	TUMOR-CELL/ft[Further Terms]
	IN-VITRO/ft[Further Terms]
	SODIUM-SALT/ft[Further Terms]
	CYTOSTATIC/ft[Further Terms]
	DOSAGE/ft[Further Terms]
	HIGH/ft[Further Terms]
	ADHESION/ft[Further Terms]
	DER./ft[Further Terms]
	MELANOMA/ft[Further Terms]
	1205LU-CELL/ft[Further Terms]
	TISSUE-CULTURE/ft[Further Terms]
	PH/ft[Further Terms]
ISSN:
	0007-4551
Language:
	French
CODEN:
	BUCABS
Date Delivered:
	20000920
Year:
	2000
Update Code:
	200000

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