Welcome to LookChem.com Sign In|Join Free

CAS

  • or

130209-76-6

Post Buying Request

130209-76-6 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

130209-76-6 Usage

Description

17-phenyl trinor PGF2α N-ethyl amide is an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug, sold under the Allergan trade name Bimatoprost. The N-ethyl amide prostaglandin prodrugs are converted to the active free acid more slowly than the analogous prostaglandin ester prodrugs such as latanoprost. This product is the isopropyl ester of the free acid prostaglandin which corresponds to Bimatoprost. The free acid, 17-phenyl trinor PGF2α, is a potent FP receptor agonist. In human and animal models of glaucoma, FP receptor agonist activity corresponds very closely with intraocular hypotensive activity. The 17-phenyl trinor PGF2α isopropyl ester derivative was examined for IOP-lowering activity during the development of latanoprost. At the dose of 3 μg/eye in the monkey, 17-phenyl trinor PGF2α isopropyl ester was the most potent analog tested in reducing IOP, lowering the IOP 1.3 mm Hg below the level achieved by latanoprost. However, this derivative was also significantly more irritating to the eye than latanoprost.

Check Digit Verification of cas no

The CAS Registry Mumber 130209-76-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,0,2,0 and 9 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 130209-76:
(8*1)+(7*3)+(6*0)+(5*2)+(4*0)+(3*9)+(2*7)+(1*6)=86
86 % 10 = 6
So 130209-76-6 is a valid CAS Registry Number.
InChI:InChI=1/C26H38O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,16-17,19,21-25,27-29H,4,9,12-15,18H2,1-2H3/b8-3-,17-16+/t21?,22-,23-,24+,25-/m1/s1

130209-76-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]hept-5-enoate

1.2 Other means of identification

Product number -
Other names Bimatoprost isopropyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:130209-76-6 SDS

130209-76-6Synthetic route

2-iodo-propane
75-30-9

2-iodo-propane

(5Z)-bimatoprost acid
38344-08-0

(5Z)-bimatoprost acid

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130209-76-6

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone for 10h; Ambient temperature;80%
15-keto-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130209-77-7

15-keto-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

A

15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130273-87-9

15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

B

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130209-76-6

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

Conditions
ConditionsYield
With sodium tetrahydroborate; cerium(III) chloride In methanol; dichloromethane for 0.5h;A 41%
B 28%
With sodium tetrahydroborate; cerium(III) chloride 1.) MeOH, CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given;
dimethyl(2-oxo-4-phenylbutyl)phosphonate
41162-19-0

dimethyl(2-oxo-4-phenylbutyl)phosphonate

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130209-76-6

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) PhB(OH)2, molecular sieves 3A, 2.) PCC, AlCl3, 3.) DIPEA, LiCl, 4.) aq. H2O2
2: 1.) CeCl3*7H2O, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C, 1 h
View Scheme
(Z)-7-((1R,2S,3R,5S)-3,5-Dihydroxy-2-hydroxymethyl-cyclopentyl)-hept-5-enoic acid isopropyl ester
177616-22-7

(Z)-7-((1R,2S,3R,5S)-3,5-Dihydroxy-2-hydroxymethyl-cyclopentyl)-hept-5-enoic acid isopropyl ester

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130209-76-6

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) PhB(OH)2, molecular sieves 3A, 2.) PCC, AlCl3, 3.) DIPEA, LiCl, 4.) aq. H2O2
2: 1.) CeCl3*7H2O, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C, 1 h
View Scheme
(Z)-7-[(1R,2S,3R,5S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dihydroxy-cyclopentyl]-hept-5-enoic acid isopropyl ester

(Z)-7-[(1R,2S,3R,5S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dihydroxy-cyclopentyl]-hept-5-enoic acid isopropyl ester

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130209-76-6

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaHSO4*H2O / tetrahydrofuran; H2O / 13 h / Ambient temperature
2: 1.) PhB(OH)2, molecular sieves 3A, 2.) PCC, AlCl3, 3.) DIPEA, LiCl, 4.) aq. H2O2
3: 1.) CeCl3*7H2O, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C, 1 h
View Scheme
Isopropyl (Z)-7-((1R,2R,3R,5S)-2-((3S,E)-3-(tert-butyldimethylsilyloxy)-5-phenyl-pent-1-enyl)-3-(tert-butyldimethylsilyloxy)-5-hydroxy-cyclopentyl)-hept-5-enoate
1190883-22-7

Isopropyl (Z)-7-((1R,2R,3R,5S)-2-((3S,E)-3-(tert-butyldimethylsilyloxy)-5-phenyl-pent-1-enyl)-3-(tert-butyldimethylsilyloxy)-5-hydroxy-cyclopentyl)-hept-5-enoate

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130209-76-6

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

Conditions
ConditionsYield
With hydrogen fluoride In water; isopropyl alcohol Product distribution / selectivity;
isobutylamine
78-81-9

isobutylamine

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130209-76-6

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

17-phenyl-trinor-prostaglandin F2α isobutylamide
1131798-25-8

17-phenyl-trinor-prostaglandin F2α isobutylamide

Conditions
ConditionsYield
In methanol at 80℃; for 24 - 48h;80%
15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130209-76-6

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

15-keto-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130209-77-7

15-keto-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 24h; Ambient temperature;76%
propylamine
107-10-8

propylamine

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130209-76-6

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
In methanol at 90℃;62%
15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130209-76-6

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

A

(Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((S)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester
177616-23-8

(Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((S)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester

B

(Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2R,3R)-3-((S)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester
177768-47-7

(Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2R,3R)-3-((S)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester

Conditions
ConditionsYield
With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; dihydrogen peroxide; phenylboronic acid Product distribution; multistep reaction; stereoselective epoxidation of 17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester and its 15-R epimer; regio- and stereoselective reactions of epoxides formed;
With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; dihydrogen peroxide; phenylboronic acid Yield given. Multistep reaction. Yields of byproduct given;
With titanium(IV) isopropylate; tert.-butylhydroperoxide; (-)-diisopropyl tartrate; dihydrogen peroxide; phenylboronic acid Yield given. Multistep reaction. Yields of byproduct given;
15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130209-76-6

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130273-87-9

15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / DDQ / dioxane / 24 h / Ambient temperature
2: 41 percent / NaBH4, CeCl3*7H2O / CH2Cl2; methanol / 0.5 h
View Scheme

130209-76-6Relevant articles and documents

Process for the Preparation of Prostaglandin Analogues and Intermediates Thereof

-

Page/Page column 22, (2009/10/21)

The present application provides intermediates for preparing prostaglandin analogues and processes for preparing prostaglandin analogues and intermediates thereof. The intermediates include: A compound of formula (6): R1 represents H, C1-C5-alkyl, or benzyl, in particular isopropyl.

Regio- and stereoselective reactions of 17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

Liljebris, Charlotta,Nilsson, Bj?rn M.,Resul, Bahram,Hacksell, Uli

, p. 4028 - 4034 (2007/10/03)

Novel prostaglandin F2α derivatives, functionalized at C13 and C14, have been prepared. 17-Phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester [(15S)-1] and its epimer [(15A)-1] were stereoselectively epoxidized, using Sharpless conditions, to produce each of the four diastereomeric epoxides (15S)-2, (15S)-3, (15R)-2, and (15R)-3. Treatment of the four epoxides with LiOH stereospecifically-produced the pentahydroxy substituted analogues 12 and 13. Alternatively, epoxides 2 and 3 were allowed to react with thiophenolate ion. The attack of the sulfur nucleophile on the epoxide occurred at either C13 or C14 depending on the stereochemistry of the epoxide and of C15.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 130209-76-6