Travoprost spectral data

Travoprost

cas 157283-68-6

[1R-[lα(Z),2β(lE,3R*),3α,5α]]-7-[3,5-Dihydroxy-2-[3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1 -butenyl]cyclopentyl]-5-heptenoic acid, 1 -methylethylester

(+)-16-m-trifluoromethylphenoxy tetranor Prostaglandin F2α isopropyl ester; (+)-Fluprostenol ispopropyl ester

(+)-(5Z,9α,1α,13E,15R)-trihydroxy-16-(3-(trifluoromethyl)phenoxy)-17,18,19,20-tetranor-prosta-5,13-dien-1-oic acid, isopropyl ester

(+) – Fluprostenol isopropyl ester,

CAS Name: (5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic acid 1-methylethyl ester

Additional Names: (+)-16-[3-(trifluoromethyl)phenoxy]-17,18,19,20-tetranorprostaglandin F2a isopropyl ester; (+)-9a,11a,15-trihydroxy-16-(3-trifluoromethylphenoxy)-17,18,19,20-tetranor-5-cis-13-trans-prostadienoic acid isopropyl ester

Manufacturers’ Codes: AL-6221

Trademarks: Travatan (Alcon)

Percent Composition: C 62.39%, H 7.05%, F 11.39%, O 19.18%

Travatan, Travatan Z, AL-6221, Travatanz, Travatan Alcon, Travatan (TN), Travatan, Travoprost, Travoprost [USAN]

Molecular Formula: C26H35F3O6

Molecular Weight: 500.54771

Alcon (Originator)

Antiglaucoma Agents, OCULAR MEDICATIONS, Ophthalmic Drugs, Prostaglandins, Prostanoid FP Agonists

Properties: Colorless oil. [a]D20 +14.6° (c = 1.0 in methylene chloride). Very sol in acetonitrile, methanol, octanol, chloroform. Practically insol in water.

Optical Rotation: [a]D20 +14.6° (c = 1.0 in methylene chloride)

Therap-Cat: Antiglaucoma.

Ophthalmic solution used for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension who are intolerant of other intraocular pressure lowering medications or insufficiently responsive (failed to achieve target IOP determined after multiple measurements over time) to another intraocular pressure lowering medication.

read at

http://newdrugapprovals.org/2014/08/02/travoprost/

Org Process Res Dev2002,6, (2): 138

http://pubs.acs.org/doi/abs/10.1021/op010097p

 (5Z,13E)-(9S,11R,15R)-9,11,15-Trihydroxy-16-(m-trifluoromethylphenoxy-17,18,19,20-tetranor-5,13-prostadienoic Acid, Isopropyl Ester (2).

The silyl-protected compound (20a+b) (202 g, 277 mmol) ………..DELETED……………………………………… All relevant fractions were combined and concentrated to give the title compound 2 (97 g, 70%) as a colourless oil,

  +14.6 (c 1.0, CH2Cl2);

 IR νmax (film) 3374 and 1727 cm-1

;1H NMR (400 MHz, CDCl3) 

δ 7.39 (1H, t, J = 8), 7.22 (1H, d, J = 8), 7.15 (1H, s), 7.08 (1H, d, J = 8), 5.70 (2H, m), 5.40 (2H, m), 4.98 (1H, heptet, J = 6.5), 4.52 (1H, m), 4.18 (1H, m), 3.97 (3H, m), 3.25 (2H, br s), 2.60 (1H, br s), 2.38 (1H, m), 2.30−1.96 (7H, m), 1.76 (1H, dd, J = 16, 4), 1.65 (2H, quintet, J = 7), 1.55 (1H, m), and 1.20 (6H, d, J = 6); 

13C NMR (100 MHz, CDCl3) 

δ 173.57, 158.67, 135.45, 131.87 (q, J = 32), 130.02, 129.85, 129.75, 128.93, 123.89 (q, J = 270), 118.06, 117.82, 111.48, 77.77, 72.70, 71.99, 70.86, 67.72, 55.82, 50.24, 42.84, 34.00, 26.60, 25.48, 24.83, and 21.81; m/z (CI) 501 (MH+, 21), 321 (34), 303 (44), and 249 (100).

BIMATOPROST SPECTRAL DATA

BIMATOPROST

155206-00-1

Lumigan, Latisse, AGN 192024, bimatoprostum, UNII-QXS94885MZ, Lumigan (TN), CHEBI:51230, AC1NSJUW, AGN-192024

Molecular Formula: C25H37NO4

 Molecular Weight: 415.56558

(Zanoni, G. et al., Tetrahedron 66, 7472-7478 (2010); Gutman, A. et al., US 20090163596 (2009)).

SYN
http://newdrugapprovals.org/2014/07/31/bimatoprost/


http://www.google.com/patents/EP2454227A1?cl=en

 BIMATOPROST97 (82.6 mg, 41% over 2 steps) as a clear, colourless oil. Analytical data consistent with the literature (Zanoni, G. et al., Tetrahedron 66, 7472-7478 (2010); Gutman, A. et al., US 20090163596 (2009)).

max (filmVcm-1 3300 (broad), 2930, 1643, 1550, 1453, 1332, 1293, 1048, 1029, 968, 729, 698

*H NMR (400 MHz; CDCI3) δΗ = 1.09 (t, J = 7.1 Hz, 3H, CH3), 1.42-2.40 (m, 14H, 6 x CH2, 2 x CH), 2.67 (m, 2H, CH2), 3.22 (dq, J = 7.1, 6.3 Hz, 2H, CH2NH), 3.41 (broad s, 3H, 3 x OH), 3.80-4.30 (broad m, 3H, 3 x CHOH), 5.37 (m, 2H, 2 x =CH), 5.47 (dd, J = 15.2, 7.9 Hz, 1H, =CH), 5.59 (dd, J = 15.2, 7.9 Hz, 1H, =CH), 5.90 (broad s, 1H, NH), 7.17 (m, 3H, ArCH’s), 7.26 (m, 2H, ArCH’s)

13C NMR ( 100 MHz; CDCI3) 5C = 14.8 (CH3), 25.4 (CH2), 25.6 (CH2), 26.7 (CH2), 31.9 (CH2), 34.4 (CH2NH), 35.8 (CH2C=0), 38.8 (CH2), 42.9 (CH2), 50.2 (CH), 55.5 (CH), 72.3 (CHOH), 72.4 (CHOH), 77.7 (CHOH), 125.8 (ArCH), 128.4 (2 x ArCH), 128.5 (2 x ArCH), 129.1 (=CH), 129.7 (=CH), 133.7 (=CH), 135.1 (=CH), 142.0 (ArC), 173.4 (C=0)

m/z (ESI+) 438.2 [MNa]+

HRMS (ESI+) calcd for Q^IV^Na [MNa]+ 438.2614, found 438.2615

[a]D 22 +41.1 (c. 0.35, CH2CI2) (lit. – Zanoni, G. et al., Tetrahedron 66, 7472-7478 (2010), +32.7 (c. 0.33, CH2CI2)) (lit. – Gutman, A. et al., US 20090163596 (2009), +36 (c. 1, MeOH))

LATANOPROST SPECTRAL DATA

Latanoprost

isopropyl-(Z)7[(1R,2R,3R,5S)3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoate.

130209-82-4

XA41, PhXA34 [as 15 (R, S) -isomer], PhXA41, Xalatan

(Zanoni, G. et al., Tetrahedron 2010, 66, 7472)

SYNTHESIS
http://newdrugapprovals.org/2014/08/02/latanoprost/


http://www.google.com/patents/WO2013186550A1?cl=en

latanoprost 77 (71 mg, 64 %) as a clear colourless oil. The IR, 13C, and optical rotation data were consistent with the literature (Zanoni, G. et al., Tetrahedron 2010, 66, 7472). Rf = 0.44 (EtOAc)

vmax (neatVcm“1 3360 (broad), 2980, 2931, 2857, 1712, 1495, 1454, 1374, 1311, 1247, 1180, 1106, 1030, 966, 910, 820, 731, 699

*H NMR (400 MHz; CDCI3) δΗ = 1.23 (6 H, d, J = 6.4 Hz, 2 x CH3), 1.30-1.90, (14 H, m, 5 x CH2, 2 x CH, 2 x OH), 2.07-2.39 (6 H, m, 3 x CH2), 2.45 (1 H, d, J = 5.5 Hz, OH), 2.63- 2.86 (2 H, m, CH2), 3.68 (1 H, br.s, CHO ), 3.95 (1 H, br.s, CHOH), 4.18 (1 H, br.s, CHO ), 5.01 (1 H, sept., J = 6.4 Hz, OCH(CH3)2), 5.35-5.52 (2 H, m, 2 x =CH), 7.16-7.24 (3 H, m, ArH’s), 7.25-7.32 (2 H, m, ArH’s)

13C NMR (125 MHz; CDCI3) 5C = 21.9 (2 x CH3), 24.9 (CH2), 26.6 (CH2), 26.8 (CH2), 29.6 (CH2), 32.1 (CH2), 34.0 (CH2), 35.7 (CH2), 39.0 (CH2), 42.5 (CH2), 51.8 (CH), 52.7 (CH), 67.6 (OCH), 71.2 (OCH), 74.5 (OCH), 78.6 (OCH), 125.7 (CH), 128.3 (2 x ArCH), 128.3 (2 x ArCH), 129.3 (CH), 129.5 (CH), 141.1 (ArC), 173.5 (C=0)

[a]D 23 33.0 (c. 1.0, MeCN) (lit, [a]D 20 32.7 (c. 1.0, MeCN))









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Decursinol angelate spectral data and interpretation

Decursinol angelate
C19H20O5
328.36

MASS


EIMS m/z 328 [M]+








1H NMR

(300MHz, CDCl3) δ 1.31, 1.33 (3H, s, gem(CH3)2), 1.77 (3H, s, 4"-H), 1.80 (3H, d, J=7.8, 5"-H), 2.83 (dd, J=17.4, 4.8, 4'-H), 3.18(1H, dd, J=17.4, 4.8, 4'-H), 5.05 (t, J=5.0, 1H, 3'-H), 6.02 (1H, q, 6.16 (1H, d, J=9.6, 3-H), 6.72 (1H, s, 5-H), 7.08 (1H, s, 8-H), 7.53 (1H, d, J=9.6, 4-H) broad line below is  ''

difficulty, then use the numbering in below fig









13 C NMR

(100MHz, CDCl3) δ 15.7 (C-4"), 20.5 (C-5"), 23.2, 25.0 (gem(CH3)2), 27.8 (C-4'), 70.0 (C-3'), 76.6 (C-2'), 104.6 (C-8), 112.8 (C-10), 113.2 (C-3), 115.8 (C-6), 127.3 (C-2"), 128.6 (C-5), 139.4 (C-3"), 143.1 (C-4), 154.2 (C-9), 156.4 (C-7), 161.2 (C-2) 167.0 (C-1")

HPLC
http://www.phcog.com/article.asp?issn=0973-1296;year=2014;volume=10;issue=37;spage=34;epage=39;aulast=Hwang

Oleanolic acid spectral data and interpretation

Oleanolic acid
(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Oleanic acid, Caryophyllin, Astrantiagenin C, Giganteumgenin C, Virgaureagenin B, 3beta-Hydroxyolean-12-en-28-oic acid, OLEANOLIC_ACID

Molecular Formula: C₃₀H₄₈O₃   

Molecular Weight: 456.70032  

Ursolic acid [(3b)-3-Hydroxyurs-12-en-28-oic acid] rarely occurs without its isomer oleanolic acid [(3b)-3-Hydroxyolean-12-en-28-oic acid] They may occur in their free acid form, as shown in Figure 1, or as aglycones for triterpenoid saponins which are comprised of a triterpenoid aglycone linked to one or more sugar moieties. Ursolic and oleanolic acids are similar in pharmacological activity

A pentacyclic triterpene that occurs widely in many PLANTS as the free acid or the aglycone for many SAPONINS. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin.   


MS
EIMS m/z (rel. int.) 456 [M]+ (5), 412 (3), 248 (100), 203 (50), 167 (25), 44 (51)


IR KBR
(KBr) 3500, 2950, 2850, 1715; 1H-NMR (250 MHz, pyridine-d5) δ: 5.49 (1H, s, H-12), 3.47 (1H, t, J = 8.0 Hz, H-3), 3.30 (1H, m, H-18), 1.12 (3H, s, CH3-27), 0.96 (3H, s, CH3-30), 0.91 (3H, s, CH3-25), 0.89 (3H, s, CH3-23), 0.87 (3H, s, CH3-24), 0.75 (3H, s, CH3-26)







1H NMR

(250 MHz, pyridine-d5) δ: 5.49 (1H, s, H-12), 3.47 (1H, t, J = 8.0 Hz, H-3), 3.30 (1H, m, H-18), 1.12 (3H, s, CH3-27), 0.96 (3H, s, CH3-30), 0.91 (3H, s, CH3-25), 0.89 (3H, s, CH3-23), 0.87 (3H, s, CH3-24), 0.75 (3H, s, CH3-26)

13 C NMR

(63 MHz, pyridine-d5) δ: 180.2 (C-28), 144.8 (C-13), 122.5 (C-12), 78.0 (C-3), 55.7 (C-5), 48.0 (C-9), 46.6 (C-8, 17), 42.1 (C-14), 39.7 (C-4), 39.4 (C-1), 37.3 (C-10), 33.2 (C-7), 32.9 (C-29), 32.4 (C-21), 30.9 (C-20), 28.7 (C-23), 27.2 (C-2), 26.9 (C-15), 26.1 (C-30), 23.7 (C-11), 23.6 (C-16), 18.7 (C-6), 17.4 (C-26), 16.5 (C-24), 15.5 (C-25)

http://www.google.com/patents/US20120237629

FIG. 4 shows the ¹H NMR spectrum of oleanolic acid;

FIG. 5 shows the ¹³C NMR spectrum of oleanolic acid;

FIG. 6 shows the ¹³C DEPT NMR spectrum of oleanolic acid;

FIG. 7 shows the ¹H ¹³C HSQC NMR spectrum of oleanolic acid;

see below

EXAMPLE 2 Extraction and Isolation of Oleanolic Acid (9) and Maslinic Acid (10) from Cloves

Syzygium aromaticum dried buds or whole cloves were obtained commercially. The cloves (1.5 kg, whole) of Syzygium aromaticum were sequentially and exhaustively extracted with hexane and ethyl acetate to give, after solvent removal in vacuo, a hexane extract (68.8 g, 4.9%) and an ethyl acetate extract (34.1 g, 2.3%). A portion of the ethyl acetate extract (10.0 g), was subjected to chromatographic separation on silica gel (60-120 mesh) column (40×5.0 cm). Elution with hexane/ethyl acetate solvent mixtures (8:2→6:4) afforded pure oleanolic acid (9) (4.7 g, 1.06%), a mixture of oleanolic acid (9) and maslinic acid (10) (0.5 g), and pure maslinic acid (10) (0.25 g). The structures of oleanolic acid (9) and maslinic acid (10) (as 2,3-diacetoxyoleanolic acid) were confirmed by spectroscopic data analysis (1D and 2D ¹H NMR and ¹³C NMR experiments) (FIGS. 4-7 and FIGS. 8-10, respectively).

3β-Acetyl-20,25-epoxydammarane-24α-ol spectral data and interpretation

3β-Acetyl-20,25-epoxydammarane-24α-ol

 C32H54O4

 502.00

IR(cm-¹)

(film) 3492, 2949, 1714, 1451, 1378, 1250, 1143, 1042, 980

1H NMR

(250 MHz, CDCl3) δ: 4.60 (1H, dd, J = 10.5, 5.5 Hz, H-3), 3.86 (1H, t, J = 7.0 Hz, H-24), 2.18 (3H, s, CH3-32), 1.17 (3H, s, CH3-27), 1.09 (3H, m, CH3-21), 1.08 (3H, s, CH3-26), 0.92 (3H, s, CH3-18), 0.83 (6H, s, CH3-28, CH3-30), 0.81 (6H, s, CH3-19, CH3-29), 0.79 (1H, m, H-5) 13 C NMR (63 MHz, CDCl3) δ: 171.5 (C-31), 86.9 (C-20), 83.7 (C-24), 81.3 (C-3), 71.9 (C-25), 56.3 (C-5), 51.1 (C-9), 50.4 (C-14), 49.9 (C-17), 43.3 (C-13), 40.8 (C-8), 38.7 (C-1), 37.9 (C-4), 37.1 (C-10), 35.7 (C-22), 35.6 (C-7), 31.9 (C-15), 30.1 (C-29), 27.9 (C-27), 27.3 (C-12), 26.1 (C-23), 24.6 (C-16), 24.1 (C-2), 24.0 (C-21), 21.9 (C-32), 21.8 (C-11), 18.5 (C-6), 16.8 (C-19, C-30), 16.7 (C-28), 15.8 (C-18)

(+)-lyoniresinol nmr

(+)-lyoniresinol

(6R,7R,8S)-8-(4-hydroxy-3,5-dimethoxyphenyl)-6,7-bis(hydroxymethyl)- 1,3-dimethoxy-5,6,7,8-tetrahydronaphthalen-2-ol

 JP2010150152

A lignan that is tetralin substituted by a 4-hydroxy-3,5-dimethoxy group at position 4, hydroxymethyl groups at positions 2 and 3, methoxy groups at positions 5 and 7 and a hydroxy group at position 6. Isolated from Machilus robusta and Sinocalamus affinis, it exhibits antineoplastic activity.


m.p(℃) 176-179

IR(cm-¹)
(KBr) 3380 (OH), 1598, 1490, 1463, 1295, 1195 (aromatic -CH=CH-)

UV(nm)
λmax 219, 278

MS
EIMS m/z 420 [M]+


1H NMR data

(300 MHz, CDCl3 + CD3OD) δ: 6.48 (1H, s, H-8), 6.32 (2H, s, H-2´, 6´), 4.11 (1H, d, J = 6.3 Hz, H-4), 3.84 (3H, s, 7-OCH3), 3.74 (6H, s, 3´, 5´-OCH3), 3.59 (1H, dd, J = 5.4, 11.1 Hz, H-2a), 3.56 (2H, t, H-3a), 3.46 (1H, dd, J = 5.4, 11.1 Hz, H-2a), 2.64 (1H, dd, J = 5.4, 15.0 Hz, H-1), 2.54 (1H, br d, J = 15.0 Hz, H-1), 1.99 (1H, m, H-3), 1.65 (1H, m, H-2)

13 C NMR

75 MHz, CDCl3 + CD3OD) 
δ: 147.8 (C-3´, 5´), 

147.4 (C-5), 

146.5 (C-7), 

138.6 (C-6), 

137.9 (C-1´),

133.5 (C-4´), 

129.4 (C-9), 

125.6 (C-10), 

107.0 (C-8), 

106.1 (C-6´, 2´), 

66.7 (C-2a), 

63.9 (C-3a), 

60.0 (5-OCH3),

56.4 (3´, 5´-OCH3), 

49.1 (C-3), 
42.5 (C-4), 

40.6 (C-2), 
33.4 (C-1)

Xiong L, Zhu C, Li Y, Tian Y, Lin S, Yuan S, Hu J, Hou Q, Chen N, Yang Y, Shi J (2011) Lignans and neolignans from Sinocalamus affinis and their absolute configurations. Journal of natural products 74, 1188-1200 [PubMed:21469695] [show Abstract]

Li Y, Cheng W, Zhu C, Yao C, Xiong L, Tian Y, Wang S, Lin S, Hu J, Yang Y, Guo Y, Yang Y, Li Y, Yuan Y, Chen N, Shi J (2011) Bioactive neolignans and lignans from the bark of Machilus robusta. Journal of natural products 74, 1444-1452 [PubMed:21627109] [show Abstract]