A convenient synthesis of pseudoceratidine and three analogs for biological evaluation

C. Behrens; M.W. Christoffersen; Lone Gram; P.H. Nielsen

doi:10.1016/S0960-894X(96)00622-1

A convenient synthesis of pseudoceratidine and three analogs for biological evaluation

C. Behrens
, M.W. Christoffersen
, Lone Gram
, P.H. Nielsen

National Institute of Aquatic Resources

Research output: Contribution to journal › Journal article › Research › peer-review

Abstract

The recently isolated marine natural product pseudoceratidine (1) has been synthesized from 2-trichloroacetylpyrrole. Bromination in the 4- and 5-position followed by nucleophilic displacement of the trichloromethyl group with spermidine gave 1 in 79% yield. The procedure is general and can easily be adopted to the preparation of other derivatives. This was demonstrated by the synthesis of a 5,5'-didebromo derivative (2) and two analogs (3-4). The compounds 1-4 have been tested for antibacterial activity and the results compared to a previous study. Also activity against the marine brine shrimp Artemia salina is reported.

Original language	English
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	7
Issue number	3
Pages (from-to)	321-326
ISSN	0960-894X
DOIs	https://doi.org/10.1016/S0960-894X(96)00622-1
Publication status	Published - 1997

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SDG 14 Life Below Water

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10.1016/S0960-894X(96)00622-1

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title = "A convenient synthesis of pseudoceratidine and three analogs for biological evaluation",

abstract = "The recently isolated marine natural product pseudoceratidine (1) has been synthesized from 2-trichloroacetylpyrrole. Bromination in the 4- and 5-position followed by nucleophilic displacement of the trichloromethyl group with spermidine gave 1 in 79\% yield. The procedure is general and can easily be adopted to the preparation of other derivatives. This was demonstrated by the synthesis of a 5,5'-didebromo derivative (2) and two analogs (3-4). The compounds 1-4 have been tested for antibacterial activity and the results compared to a previous study. Also activity against the marine brine shrimp Artemia salina is reported.",

author = "C. Behrens and M.W. Christoffersen and Lone Gram and P.H. Nielsen",

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doi = "10.1016/S0960-894X(96)00622-1",

language = "English",

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journal = "Bioorganic \& Medicinal Chemistry Letters",

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T1 - A convenient synthesis of pseudoceratidine and three analogs for biological evaluation

AU - Behrens, C.

AU - Christoffersen, M.W.

AU - Gram, Lone

AU - Nielsen, P.H.

PY - 1997

Y1 - 1997

N2 - The recently isolated marine natural product pseudoceratidine (1) has been synthesized from 2-trichloroacetylpyrrole. Bromination in the 4- and 5-position followed by nucleophilic displacement of the trichloromethyl group with spermidine gave 1 in 79% yield. The procedure is general and can easily be adopted to the preparation of other derivatives. This was demonstrated by the synthesis of a 5,5'-didebromo derivative (2) and two analogs (3-4). The compounds 1-4 have been tested for antibacterial activity and the results compared to a previous study. Also activity against the marine brine shrimp Artemia salina is reported.

AB - The recently isolated marine natural product pseudoceratidine (1) has been synthesized from 2-trichloroacetylpyrrole. Bromination in the 4- and 5-position followed by nucleophilic displacement of the trichloromethyl group with spermidine gave 1 in 79% yield. The procedure is general and can easily be adopted to the preparation of other derivatives. This was demonstrated by the synthesis of a 5,5'-didebromo derivative (2) and two analogs (3-4). The compounds 1-4 have been tested for antibacterial activity and the results compared to a previous study. Also activity against the marine brine shrimp Artemia salina is reported.

U2 - 10.1016/S0960-894X(96)00622-1

DO - 10.1016/S0960-894X(96)00622-1

M3 - Journal article

SN - 0960-894X

VL - 7

SP - 321

EP - 326

JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 3

ER -

A convenient synthesis of pseudoceratidine and three analogs for biological evaluation

Abstract

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