Propanamide,2-amino-N-[(3S,4R,4aR,5R,6R)-3-(dichloromethyl)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl]-,(2S)-

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Names

[ CAS No. ]:
72615-20-4

[ Name ]:
Propanamide,2-amino-N-[(3S,4R,4aR,5R,6R)-3-(dichloromethyl)-3,4,4a,5,6,7-hexahydro-5,6,8-trihydroxy-3-methyl-1-oxo-1H-2-benzopyran-4-yl]-,(2S)-

[Synonym ]:
bactobolin A
BN 183B
Bactobolin
Antibiotic BN 183B

Chemical & Physical Properties

[ Density]:
1.55g/cm3

[ Boiling Point ]:
642.9ºC at 760 mmHg

[ Molecular Formula ]:
C14H20Cl2N2O6

[ Molecular Weight ]:
383.22400

[ Flash Point ]:
342.6ºC

[ Exact Mass ]:
382.07000

[ PSA ]:
142.11000

[ LogP ]:
0.58260

[ Index of Refraction ]:
1.613

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CP1315000
CHEMICAL NAME :
Bactobolin
CAS REGISTRY NUMBER :
72615-20-4
LAST UPDATED :
199309
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C14-H20-Cl2-N2-O6
MOLECULAR WEIGHT :
383.26

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
6250 ug/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 33,1054,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
10 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JOPHDQ Journal of Pharmacobio-Dynamics. (Japan Pub. Trading Co. (USA), 1255 Howard St., San Francisco, CA 94103) V.1- 1978- Volume(issue)/page/year: 3,177,1980

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • endo-(+/-)-N-(3-oxo-2-oxabicyclo[3.3.1]non-6-en-4-yl)-2-(trimethylsilyl)ethanesulfonamide
  • N-((1R,6R,9R)-8-oxo-3,7-dioxatricyclo[4.3.1.02,4]decan-9-yl)-2-(trimethylsilyl)ethanesulfonamide
  • N-((1S,4S,5S,6S,7S)-6,7-dihydroxy-3-oxo-2-oxabicyclo[3.3.1]nonan-4-yl)-2-(trimethylsilyl)ethanesulfonamide
  • N-[1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-oxopropyl]-2-(trimethylsilyl)ethanesulfonamide
  • N-[3,3-dichloro-1-(hexahydro-6-hydroxy-2,2-dimethyl-1,3-benzodioxol-4-yl)-2-hydroxy-2-methylpropyl]-2-(trimethylsilyl)ethanesulfonamide
  • (S)-2-((3aS,4S,6S,7aS)-6-hydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxol-4-yl)-N-methoxy-N-methyl-2-(2-(trimethylsilyl)ethylsulfonamido)acetamide
  • N-[3,3-dichloro-1-(hexahydro-2,2-dimethyl-6-oxo-1,3-benzodioxol-4-yl)-2-methylpropyl]-2-(trimethylsilyl)ethanesulfonamide
  • N-[8-(dichloromethyl)-3a,4,8,9,9a,9b-hexahydro-5-hydroxy-2,2,8-trimethyl-6H-1,3-dioxolo[4,5-f][2]benzopyran-9-yl]-2-(trimethylsilyl)ethanesulfonamide

DownStream

Related Compounds

  • N-(1-([1,2,4]triazolo[4,3-b]pyridazin-6-yl)azetidin-3-yl)-4-(2,5-dioxopyrrolidin-1-yl)-N-methylbenzenesulfonamide
  • 1-(3,4-dimethylphenyl)-3-((4-(thiophen-3-yl)tetrahydro-2H-pyran-4-yl)methyl)urea
  • N'-[(4-fluorophenyl)methyl]-N-{[4-(thiophen-3-yl)oxan-4-yl]methyl}ethanediamide
  • 1-(4-methoxybenzyl)-3-((4-(thiophen-3-yl)tetrahydro-2H-pyran-4-yl)methyl)urea
  • 1-(2-fluorophenyl)-N-((4-(thiophen-3-yl)tetrahydro-2H-pyran-4-yl)methyl)methanesulfonamide
  • N-(2-methoxy-5-methylphenyl)-N'-{[4-(thiophen-3-yl)oxan-4-yl]methyl}ethanediamide
  • 1-(3-methylphenyl)-N-{[4-(thiophen-3-yl)oxan-4-yl]methyl}methanesulfonamide
  • N1-(2-(methylthio)phenyl)-N2-((4-(thiophen-3-yl)tetrahydro-2H-pyran-4-yl)methyl)oxalamide
  • N-(2H-1,3-benzodioxol-5-yl)-N'-{[4-(thiophen-3-yl)oxan-4-yl]methyl}ethanediamide
  • N'-(3-chloro-4-fluorophenyl)-N-{[4-(thiophen-3-yl)oxan-4-yl]methyl}ethanediamide