74618-46-5

Upstream product

• 67123-97-1 (R,S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 108-24-7 acetic anhydride 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 143767-54-8 (R,S)-2-acetyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 
• 75-36-5 acetyl chloride 
• 41994-51-8 1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid ; hydrochloride 

Relevant academic research and scientific papers

Novel bifunctional alkylating agents, 5,10-dihydropyrrolo[1,2-b] isoquinoline derivatives, synthesis and biological activity

A series of linear pyrrolo[1,2-b]isoquinoline derivatives was synthesized for antitumor evaluation. The preliminary antitumor studies reveal that both bis(hydroxymethyl) and their bis(alkylcarbamate) derivatives show significant antitumor activity in inhibiting various human tumor cell growth in vitro. 1,2-Bis(hydroxymethyl)-3-methyl-5,10-dihydropyrrolo[1,2-b]isoquinoline (20a) was selected for antitumor studies in animal models. The results show that this agent can induce complete tumor remission or significant suppression in nude mice bearing human breast (MX-1) xenograft and ovarian (SK-OV-3) xenografts, respectively. Alkaline agarose gel shifting assay showed that 20a is able to cross-link with DNA. Studies on the cell cycle inhibition revealed that this agent induces cell arrest at G2/M phase. The results warrant further antitumor investigation against other human tumor growth in animal models.

SYNTHESIS OF 8H-3A-AZA-CYCLOPENTA[A]INDENES AND 5,10-DIHYDROPYRROLO[1,2-B]ISOQUINOLINES DERIVATIVES AND THEIR USE AS ANTITUMOR THERAPEUTIC AGENTS

The present disclosure relates to a series of bis(hydroxymethyl) and its bis(carbamate) of 8H-3a-azacyclopenta[a]indene-1-yl and 5,10-dihydropyrrolo-[1,2-b]isoquinolines derivatives (Formula I-Formula IV) as DNA di-alkylating agents. The preliminary antitumor studies indicated that compounds disclosed herein could exhibit potent cytotoxicity in vitro and antitumor therapeutic efficacy in human tumor xenografts and could have little or no cross-resistance to either Taxol or Vinblastine. The results demonstrated that compounds disclosed herein possess potent antitumor therapeutic efficacy and are expected to have potential for clinical applications.

The Intramolecular 1,3-Dipolar Cyclisation of Mesoionic Species Generated by the Thermolysis of the Mixed Anhydrides of Acetic and N-Alkynoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acids

The intramolecular cyclisations of mesoionic intermediates formed by heating N-alkynoyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids C-(CH2)nCO, where n = 3 or 4> with acetic anhydride, have been investigated.The final products are octahydropentalenoisoquinolines and hexahydroindenoisoquinolines, respectively, formed by the expulsion of carbon dioxide from the initial adducts.The behaviour of alkenes and alkynes as dienophiles in intermolecular versions of the cycloaddition reactions have also been studied.Alkynes bearing electron withdrawing groups afford pyrroloisoquinolines, but unless alkenes, such as benzylidenemalonodinitrile are used (where the first formed adduct can eliminate HCN, prior to loss of CO2), the reactions fail.

The Synthesis of Polycyclic Benz-Fused Pyrroles (1)

Pyrrolophenanthridine (2), benzopyrroloisoquinoline (3), 5,6,7,8,9,10,11-hexahydrobenzopyrroloisoquinoline (5), and pyrroloisoquinoline (6) dicarboxylic acid diesters were prepared in 1,3-dipolar cycloaddition reactions between dimethyl acetylenedicarboxylate and the hydrofluoroborate salt of the appropriate Reissert compound.Several of the different methods to prepare Reissert compounds are compared and the carbon-13 nmr spectra for the Reissert compounds are reported.Carbon-13 nmr was used to assign the structures of isomers 10 and 11; the latter compounds arose from a prior reaction in which the cyclization of β-(5,6,7,8-tetrahydro-2-naphthyl)ethylamine N-formate which gave a mixture of hexahydroisoquinolines, 8a and 9a.Pyrroloisoquinoline (12) and pyrroloisoquinoline dicarboxylic acid diesters were made in muenchnone cycloaddtition reactions.The latter compound was made from tetrahydroisoquinoline-1-carboxylic acid which was readily prepared from isoquinaldic acid by catalytic reduction.The dehydrogenation of several of the partially saturated compounds is also discussed.