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Cyclomarin A

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Identification
Molecular formula
C40H56BrN7O7
CAS number
156098-30-9
IUPAC name
(6aR,9R)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-isobutyl-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
State
State
Cyclomarin A is typically solid at room temperature. It is usually handled in its purified form as a research compound in biochemical laboratories.
Melting point (Celsius)
235.00
Melting point (Kelvin)
508.15
Boiling point (Celsius)
320.00
Boiling point (Kelvin)
593.15
General information
Molecular weight
643.83g/mol
Molar mass
643.8310g/mol
Density
1.3000g/cm3
Appearence

Cyclomarin A typically appears as a crystalline powder and may have a light yellowish to off-white coloration. It is often studied in a purified form for biochemical research and displays the typical appearance of organic compounds in solid crystalline form.

Comment on solubility

Solubility of (6aR,9R)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-isobutyl-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

The solubility of a compound is a critical factor influencing its bioavailability and practical applications. In the case of (6aR,9R)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-isobutyl-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide, the solubility may exhibit the following characteristics:

  • Polarity: Given the presence of multiple functional groups, including hydroxyl and dioxo structures, this compound may demonstrate variable polarity, affecting its solubility in both polar and non-polar solvents.
  • Hydrogen Bonding: The hydroxyl groups can form hydrogen bonds, potentially enhancing solubility in polar solvents such as water and alcohols.
  • Intermolecular Interactions: The complex structure could lead to significant intermolecular interactions, influencing the compound’s behavior in different mediums.
  • Temperature Variability: Like many compounds, solubility can be temperature-dependent, usually increasing with higher temperatures for organic compounds.

Overall, one might expect that the solubility of this compound could vary significantly based on the solvent used. As a helpful guiding principle, “like dissolves like” applies here, indicating that the solubility will be better in solvents with similar polarities. Additional experimentation is recommended to accurately determine its solubility profile in various contexts.

Interesting facts

Interesting Facts about (6aR,9R)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-isobutyl-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide

This intricate compound represents a fascinating blend of structural complexity and potential biological activity. It belongs to a class of chemical compounds known for their diverse medicinal properties, making it a valuable subject of research in pharmacology and medicinal chemistry.

Chemical Structure and Uniqueness

  • Complexity: The compound exhibits a highly complex multi-cyclic structure, featuring various functional groups that may contribute to its biological interactions.
  • Chirality: The presence of multiple chiral centers indicates that the compound has stereoisomeric forms, which can result in different biological activities.
  • Diversity: Within its structure, the incorporation of both indole and quinoline rings highlights the versatility of this compound. These moieties are frequently found in naturally occurring compounds and are often associated with pharmacophores.

Potential Applications

The compound's unique structural composition suggests several potential applications:

  • Antimicrobial Activity: Many compounds with similar structures have shown effectiveness against various pathogens, making this compound a candidate for further exploration in the fight against infectious diseases.
  • Anti-cancer Properties: Compounds of this nature have been studied for their ability to influence cancer cell signaling pathways, which could pave the way for new anticancer therapies.
  • Neuroprotective Effects: The indole structure is known for its role in modulating neurotransmitter systems, hinting at potential applications in neuropharmacology.

As noted by researchers, "The activity of compounds with diverse functionalities can often yield a wide array of therapeutic possibilities." This statement rings true for the compound in question, highlighting its importance in ongoing scientific investigations.

Ongoing research may reveal even more about this compound's mechanisms and potential, showcasing just how multifaceted and rich the field of organic chemistry can be. The journey of discovery in this domain is often filled with astonishing surprises!

Synonyms
bromocriptine
25614-03-3
Bromoergocryptine
Bromocriptin
Bromergocryptine
Bromoergocriptine
Bromocriptina
2-Bromo-alpha-ergocryptine
Bromocriptinum
Ergoset
2-Bromo-alpha-ergokryptin
2-Bromo-alpha-ergokryptine
Ergocryptine, 2-bromo-
2-Bromoergocryptine
(+)-Bromocriptine
3A64E3G5ZO
CHEBI:3181
DTXSID1022687
SANDOZ 15-754
Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'alpha)-
DTXCID602687
(5'alpha)-2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-3',6',18-trioxoergotaman
(5'alpha)-2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)ergotaman-3',6',18-trione
Bromocryptin
(5'alpha)-2-bromo-12'-hydroxy-5'-isobutyl-2'-isopropyl-3',6',18-trioxoergotaman
(6aR,9R)-5-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
2-Bromoergokryptine
2 Bromo alpha ergocryptine
(4R,7R)-10-bromo-N-((1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo(7.3.0.0^(2,6))dodecan-4-yl)-6-methyl-6,11-diazatetracyclo(7.6.1.0^(2,7).0^(12,16))hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
(4R,7R)-10-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
(6aR,9R)-5-bromo-N-((1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo(7.3.0.02,6)dodecan-4-yl)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo(4,3-fg)quinoline-9-carboxamide
2 Bromoergocryptine
2 Bromoergokryptine
RefChem:56423
2 Bromo alpha ergokryptine
G02CB01
N04BC01
CB154
Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'alpha-(2-methylpropyl)-
(4R,7R)-10-bromo-N-((1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo(7.3.0.02,6)dodecan-4-yl)-6-methyl-6,11-diazatetracyclo(7.6.1.02,7.012,16)hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
247-128-5
Bromocryptine
Bromocriptinum [INN-Latin]
Bromocriptina [INN-Spanish]
CB-154
Bromocriptine (mesylate)
Bromergon
Ergotaman-3',6',18-trione, 2-bromo-12'-hydroxy-2'-(1-methylethyl)-5'-(2-methylpropyl)-, (5'.alpha.)-
2-Bromo-.alpha.-ergocryptine
CCRIS 3244
NSC169774
EINECS 247-128-5
Bromocriptine (USAN/INN)
UNII-3A64E3G5ZO
Bromokryptine
SR-01000075356
Bromocriptine [USAN:INN:BAN]
NCGC00024584-03
08Y
2-Bromo-12'-hydroxy-2'-(1-methylethyl)-5'-alpha-(2-methylpropyl)ergotamin-3',6',18-trione
Bromocriptine+ (GTP-)
Prestwick0_000121
Prestwick1_000121
Prestwick2_000121
BROMOCRIPTINE [MI]
Biomol-NT_000005
CHEMBL493
GTPL35
BROMOCRIPTINE [INN]
BROMOCRIPTINE [USAN]
Lopac0_000171
SCHEMBL25297
BROMOCRIPTINE [VANDF]
BIDD:GT0464
SPBio_002101
BROMOCRIPTINE [WHO-DD]
BPBio1_001131
SCHEMBL29364057
BDBM81993
Tox21_110907
PDSP2_001500
AKOS015961273
CCG-204266
DB01200
SDCCGSBI-0050159.P003
NCGC00024584-04
NCGC00024584-05
NCGC00024584-07
NCGC00024584-09
NCGC00024584-17
(5'alpha)-2-bromo-12'-hydroxy-5'-(2-methylpropyl)-2'-(propan-2-yl)-3',6',18-trioxoergotaman
(6aR,9R)-5-Bromo-N-((2R,5S,10aS,10bS)-10b-hydroxy-5-isobutyl-2-isopropyl-3,6-dioxooctahydro-2H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
AC-13601
AC-37665
DA-61890
NCI60_001365
CAS-25614-03-3
CS-0012283
NS00001292
C06856
D03165
EN300-19768234
Q413581
SR-01000075356-5
BRD-K14496212-001-01-1
BRD-K14496212-066-02-2
BRD-K14496212-066-04-8
SAN 15-754; Sandoz 15-754; -Bromocryptine; -Bromoergocryptine; -Ergolactin
(4R,7R)-10-bromo-N-[(1S,2S,4R,7S)-2-hydroxy-7-(2-methylpropyl)-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0^{2,6}]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide
(5alpha,5'beta)-2-bromo-12'-hydroxy-5'-(2-methylpropyl)-3',6',18-trioxo-2'-(propan-2-yl)ergotaman
N-[(2R,5S,10aS,10bS)-10b-hydroxy-5-isobutyl-2-isopropyl-3,6-dioxo-8,9,10,10a-tetrahydro-5H-oxazolo[[?]]pyrrolo[[?]]pyrazin-2-yl]-bromo-methyl-[?]carboxamide