105372-81-4

Basic information

• Product Name: 2',3',5',7',8',9'-Hexahydro-3,5-dibromospiro[2,5-cyclohexadiene-1,10'(6'H)-pyrrolo[4,3,2-de][1,7]phenanthroline]-4,6'-dione
• Synonyms: 2',3',5',7',8',9'-Hexahydro-3,5-dibromospiro[2,5-cyclohexadiene-1,10'(6'H)-pyrrolo[4,3,2-de][1,7]phenanthroline]-4,6'-dione;Discorhabdin C;Discorhabdine C
• CAS NO: 105372-81-4
• Molecular Formula: C18H13Br2N3O2
• Molecular Weight: 463.12272
• Mol File: 105372-81-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 717.0±60.0 °C(Predicted)
• Appearance: /
• Density: 2.11±0.1 g/cm3(Predicted)
• PKA: 14.92±0.60(Predicted)
• CAS DataBase Reference: 2',3',5',7',8',9'-Hexahydro-3,5-dibromospiro[2,5-cyclohexadiene-1,10'(6'H)-pyrrolo[4,3,2-de][1,7]phenanthroline]-4,6'-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3',5',7',8',9'-Hexahydro-3,5-dibromospiro[2,5-cyclohexadiene-1,10'(6'H)-pyrrolo[4,3,2-de][1,7]phenanthroline]-4,6'-dione(105372-81-4)
• EPA Substance Registry System: 2',3',5',7',8',9'-Hexahydro-3,5-dibromospiro[2,5-cyclohexadiene-1,10'(6'H)-pyrrolo[4,3,2-de][1,7]phenanthroline]-4,6'-dione(105372-81-4)

Safety Data

• Hazardous Substances Data: 105372-81-4(Hazardous Substances Data)

Upstream product

• 137022-91-4 7-<<2-(3,5-dibromo-4-hydroxyphenyl)ethyl>amino>-1,3,4,8-tetrahydropyrrolo<4,3,2-de>quinolin-8-one 
• 220034-67-3 N-tosyldiscorhabdin C 
• 15969-08-1 6-methoxy-2-nitrophenol 
• 70978-05-1 3-methoxy-2-(benzyloxy)benzenamine 
• 100245-10-1 2-Benzyloxy-1-methoxy-3-nitro-benzene 
• 161156-09-8 {2-[6-Methoxy-4,7-dioxo-1-(toluene-4-sulfonyl)-4,7-dihydro-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester 
• 220034-72-0 2-Benzyloxy-6-iodo-3-methoxy-phenylamine 
• 220034-61-7 (7-Benzyloxy-6-methoxy-1H-indol-3-yl)-acetonitrile 
• 220034-60-6 (E)-4-(2-Benzyloxy-6-iodo-3-methoxy-phenylamino)-but-2-enenitrile 
• 220034-73-1 [2-(7-Benzyloxy-6-methoxy-1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester 
• 220034-63-9 {2-[7-Hydroxy-6-methoxy-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester 
• 220034-64-0 7-(3,5-dibromo-4-hydroxyphenethylamino)-1-tosyl-3,4-dihydropyrrolo[4,3,2-de]quinolin-8(1H)-one 
• 220034-62-8 {2-[7-Benzyloxy-6-methoxy-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester 
• 105908-35-8 6,7-dimethoxy-4-methylquinoline 

Relevant articles and documents

A biomimetic approach to the discorhabdin alkaloids: Total syntheses of discorhabdins C and E and dethiadiscorhabdin D

The characteristic spirodienone structure of the discorhabdin alkaloids is readily formed by reaction of the tyramine-substituted indoloquinonimines 26, 35, and 36 with cupric chloride, triethylamine, and oxygen. This cyclization provides a possibly biomimetic route to discorhabdins C and E (41 and 42). The unbrominated spirodienone 40 reacts with hydrogen over Pd/C to give enone 46. Bromination at the α position gives a mixture of bromoenones that undergo smooth conversion to dethiadiscorhabdin D (4) upon treatment with basic alumina.

Synthetic studies on tetrahydropyrroloquinoline-containing natural products: Syntheses of discorhabdin C, batzelline C and isobatzelline C

Discorhabdin C (1), batzelline C (2) and isobatzelline C (3), metabolites of marine sources sharing a tetrahydropyrroloquinoline core, have been successfully synthesized, and cytotoxicities of several synthetic intermediates were evaluated.

Synthetic studies on novel sulfur-containing alkaloids, prianosins and discorhabdins: Total synthesis of discorhabdin C

The first total synthesis of discorhabdin C, related to the cytotoxic sulfur-containing alkaloids prianosins and discorhabdins is described. The crucial phenolic oxidation of the appropriate phenol carrying no protective group was achieved by electrochemi