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Tigecycline
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Name

Tigecycline

 EINECS 685-736-6
CAS No. 220620-09-7 Density 1.455 g/cm3
PSA 205.76000 LogP 1.67740
Solubility N/A Melting Point 164-166°C
Formula C29H39N5O8 Boiling Point 890.922 °C at 760 mmHg
Molecular Weight 585.657 Flash Point 492.612 °C
Transport Information N/A Appearance Powder
Safety 24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 220620-09-7 (Tigecycline) Hazard Symbols N/A
Synonyms

2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-((((1,1-dimethylethyl)amino)acetyl)amino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-;N-[(5aR,6aS,7S,9Z,10aS)-9-(amino-hydroxy-methylidene)-4,7-bis(dimethylamino)-1,10a,12-trihydroxy-8,10,11-trioxo-5a,6,6a,7-tetrahydro-5H-tetracen-2-yl]-2-(tert-butylamino)acetamide;Tygacil (TN);Tygacil;(4S,4aS,5aR,12aS)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide;

Article Data 16

Tigecycline Synthetic route

156263-28-4

9-chloroacetamidominocycline

75-64-9

tert-butylamine

220620-09-7

tigecycline

Conditions
ConditionsYield
With sodium iodide In N,N-dimethyl acetamide at 50℃; for 2h;92%
Stage #1: 9-chloroacetamidominocycline; tert-butylamine With sodium iodide at 20℃;
Stage #2: In water pH=5 - ~ 7.2; Product distribution / selectivity;		50%
With sodium iodide at 25 - 40℃; for 6h; Product distribution / selectivity;

2-(t-butylamino)acetyl chloride hydrochloride

9-amino-7-(dimethylamino)doxycycline hydrochloride

220620-09-7

tigecycline

Conditions
ConditionsYield
In water at 0 - 5℃; for 2h;90%

2-(t-butylamino)acetyl chloride hydrochloride

<4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide monohydrochloride

220620-09-7

tigecycline

Conditions
ConditionsYield
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; <4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide monohydrochloride In water at 0 - 6℃; for 1h; Industry scale;
Stage #2: With hydrogenchloride; ammonia In methanol; dichloromethane; water at 0 - 25℃; pH=0.42 - 7.4; Product distribution / selectivity;		77%
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; <4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide monohydrochloride In water at 0 - 6℃; for 1h; Industry scale;
Stage #2: With hydrogenchloride; ammonia In methanol; dichloromethane; water at 0 - 25℃; pH=0.42 - 7.4; Product distribution / selectivity;		77%
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; <4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide monohydrochloride In water at 0 - 6℃; for 1h; Industry scale;
Stage #2: With hydrogenchloride; ammonia In methanol; dichloromethane; water at 0 - 25℃; pH=0.42 - 7.4; Product distribution / selectivity;		77%

2-(t-butylamino)acetyl chloride hydrochloride

149934-19-0

[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

220620-09-7

tigecycline

Conditions
ConditionsYield
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide In water at 0 - 5℃; for 0.666667 - 1h;
Stage #2: With ammonia In water at 0 - 5℃; pH=7.2; Product distribution / selectivity;		76.8%
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide In water at 0 - 5℃; for 0.666667 - 1h;
Stage #2: With ammonia In methanol; dichloromethane; water at 0 - 5℃; for 0.25h; pH=7.2; Product distribution / selectivity;		76.8%
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide In water at 0 - 5℃; for 0.666667 - 1h;
Stage #2: With ammonia In methanol; dichloromethane; water at 0 - 5℃; for 0.25h; pH=7.2; Product distribution / selectivity;		76.8%

9-chloroacetamidominocycline hydrochloride

75-64-9

tert-butylamine

220620-09-7

tigecycline

Conditions
ConditionsYield
Stage #1: 9-chloroacetamidominocycline hydrochloride; tert-butylamine With sodium iodide at 20℃;
Stage #2: In water pH=5 - ~ 7.2; Product distribution / selectivity;		35%
7065-46-5

3,3-dimethylbutanoic acid chloride

149934-19-0

[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

220620-09-7

tigecycline

156263-28-4

9-chloroacetamidominocycline

75-64-9

tert-butylamine

A

Epitigecycline

B

220620-09-7

tigecycline

Conditions
ConditionsYield
With sodium iodide at 33 - 38℃; for 4h; Product distribution / selectivity;

2-(t-butylamino)acetyl chloride hydrochloride

149934-19-0

[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

A

Epitigecycline

B

220620-09-7

tigecycline

Conditions
ConditionsYield
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide In water at 0 - 5℃; for 0.666667 - 1h;
Stage #2: With ammonia In water at 0 - 5℃; pH=7.2; Product distribution / selectivity;
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide In dichloromethane at 10 - 15℃; for 2h;
Stage #2: With ammonia In methanol; dichloromethane; water at 5 - 8℃; pH=7.2; Product distribution / selectivity;
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide In N,N-dimethyl-formamide at 10 - 15℃; for 2h;
Stage #2: With ammonia In methanol; water; N,N-dimethyl-formamide at 5 - 8℃; pH=7.2; Product distribution / selectivity;

2-(t-butylamino)acetyl chloride hydrochloride

<4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide monohydrochloride

A

Epitigecycline

B

220620-09-7

tigecycline

Conditions
ConditionsYield
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; <4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide monohydrochloride In water at 0 - 6℃; for 1 - 3h;
Stage #2: With ammonia In water at 0 - 10℃; pH=7.2; Product distribution / selectivity;

2-(t-butylamino)acetyl chloride hydrochloride

<4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide disulfate

220620-09-7

tigecycline

Conditions
ConditionsYield
Stage #1: <4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide disulfate With sodium carbonate In water at 0℃; pH=2 - 3; Inert atmosphere;
Stage #2: 2-tert-butylaminoacetylchloride hydrochloride With sodium carbonate In water at 0 - 30℃; pH=6.7; Inert atmosphere;

Tigecycline Specification

1.  Introduction of Tigecycline

Tigecycline, with its CAS NO.220620-09-7, is a kind of orange Powder. Its Synonyms are 2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-((((1,1-dimethylethyl)amino)acetyl)amino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)- ; Tygacil ; (4S,4aS,5aR,12aS)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide . Tigecycline is bacteriostatic and is a protein synthesis inhibitor by binding to the 30S ribosomal subunit of bacteria and thereby blocking entry of Aminoacyl-tRNA into the A site of the ribosome during prokaryotic translation.

2. Properties of Tigecycline

(1) XLogP3: -0.2  (2) H-Bond Donor: 7  (3) H-Bond Acceptor: 12
(4) Surface Tension: 80.036 dyne/cm (5) Density: 1.455 g/cm3 (6) Flash Point: 492.612 °C
(7) Enthalpy of Vaporization: 135.666 kJ/mol (8) Boiling Point: 890.922 °C at 760 mmHg

3. Structure descriptors of Tigecycline

IUPAC Name: (4S,4aS,5aR,12aR)-9-[[2-(tert-butylamino)acetyl]amino]-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,
6-tetrahydro-4H-tetracene-2-carboxamide

InChI: InChI=1S/C29H39N5O8/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36/h10,12,14,21,31,36-37,40,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21-,29-/m0/s1

InChIKey: SOVUOXKZCCAWOJ-HJYUBDRYSA-N

Canonical SMILES : CC(C)(C)NCC(=O)NC1=C(C2=C(CC3CC4C(C(=O)C(=C(C4(C(=O)C3=C2O)O)O)C(=O)N)N(C)C)C(=C1)N(C)C)OIsomeric SMILES: CC(C)(C)NCC(=O)NC1=C(C2=C(C[C@H]3C[C@H]4[C@@H](C(=O)C(=C([C@]4(C(=O)C3=
C2O)O)O)C(=O)N)N(C)C)C(=C1)N(C)C)O
 

4. Uses of Tigecycline

Tigecycline is active against many bacteria including Gram-positive bacteria, Gram-negative bacteria and anaerobes ,it also has activity against methicillin-resistant Staphylococcus aureus (MRSA) and multi-drug resistant strains of Acinetobacter baumannii. It may have no activity against Pseudomonas spp. or Proteus spp. The drug is licenced for the treatment of skin,soft tissue infections ,and intra-abdominal infections.
 

 

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