methyl 6-[(3S,6S,9S,12R)-3-butan-2-yl-6-[(1-methoxyindol-3-yl)methyl]-2,5,8,11-tetraoxo-1,4,7,10-tetrazabicyclo[10.4.0]hexadecan-9-yl]hexanoate

Base Information

Chemical Name:methyl 6-[(3S,6S,9S,12R)-3-butan-2-yl-6-[(1-methoxyindol-3-yl)methyl]-2,5,8,11-tetraoxo-1,4,7,10-tetrazabicyclo[10.4.0]hexadecan-9-yl]hexanoate
CAS No.:183506-66-3
Molecular Formula:C34H49N5O6
Molecular Weight:623.793
Hs Code.:29419090
Mol file:183506-66-3.mol

methyl 6-[(3S,6S,9S,12R)-3-butan-2-yl-6-[(1-methoxyindol-3-yl)methyl]-2,5,8,11-tetraoxo-1,4,7,10-tetrazabicyclo[10.4.0]hexadecan-9-yl]hexanoate

Synonyms:apicidin;apicidin C;cyclo(N-O-methyl-tryptophyl-isoleucyl-pipecolinyl-2-amino-8-oxodecanoyl)

Suppliers and Price of methyl 6-[(3S,6S,9S,12R)-3-butan-2-yl-6-[(1-methoxyindol-3-yl)methyl]-2,5,8,11-tetraoxo-1,4,7,10-tetrazabicyclo[10.4.0]hexadecan-9-yl]hexanoate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Usbiological
Apicidin
1mg
$ 329.00

Usbiological
Apicidin
1mg
$ 290.00

Usbiological
Apicidin
2mg
$ 390.00

Usbiological
Apicidin
2.5mg
$ 516.00

TRC
Apicidin
25mg
$ 1505.00

Sigma-Aldrich
Apicidin ≥98% (HPLC), from microbial
5mg
$ 390.00

Sigma-Aldrich
Apicidin ≥98% (HPLC), from microbial
1mg
$ 113.00

ChemScene
Apicidin ≥99.0%
1mg
$ 220.00

Cayman Chemical
Apicidin ≥90%
5mg
$ 188.00

Cayman Chemical
Apicidin ≥90%
1mg
$ 47.00

Total 33 raw suppliers

Chemical Property of methyl 6-[(3S,6S,9S,12R)-3-butan-2-yl-6-[(1-methoxyindol-3-yl)methyl]-2,5,8,11-tetraoxo-1,4,7,10-tetrazabicyclo[10.4.0]hexadecan-9-yl]hexanoate

Chemical Property:

Appearance/Colour:Solid
Refractive Index:1.615
PKA:13.09±0.70(Predicted)
PSA：138.84000
Density:1.27g/cm³
LogP:4.12130
Storage Temp.:−20°C
Solubility.:DMSO: ~1mg/mL
XLogP3:4.1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:12
Exact Mass:625.34754886
Heavy Atom Count:45
Complexity:1060

Purity/Quality:

99%, ^*data from raw suppliers

Apicidin ^*data from reagent suppliers

Safty Information:

Pictogram(s): T+
Hazard Codes:T+
Statements: 26/27/28
Safety Statements: 22-26-36/37/39-45

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CCC(C)C1C(=O)N2CCCCC2C(=O)NC(C(=O)NC(C(=O)N1)CC3=CN(C4=CC=CC=C43)OC)CCCCCC(=O)OC
Isomeric SMILES:CCC(C)[C@H]1C(=O)N2CCCC[C@@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC3=CN(C4=CC=CC=C43)OC)CCCCCC(=O)OC
Description Apicidin (183506-66-3) is a fungal toxin that is a potent, cell permeable inhibitor of histone deacetylases (HDAC’s).1?It also displays antitumor properties by inducing changes in p21WAF1/Cip1 and gelsolin gene expression causing cell cycle arrest in the G1?phase.2?Apicidin dramatically decreases HIF-1α protein levels and transcriptional activity in human and mouse tumor cell lines.3
Uses Apicidin is a potent (nM) cell permeable inhibitor of histone deacetylase. Also, Apicidin exhibits antiprotozoal and potential antimalarial properties. Apicidin has antiproliferative activity on HeLa cells accompanied by cell arrest at the G1 phase. Apicidin induces selective changes in the expression of p21 and gelsolin. Apicidin is a cyclic peptide antibiotic with broad spectrum antiparasitic and antiprotozoan activity. Apicidin, a histone deacetylase inhibitor, is anti-angiogenic and induces apoptosis. Apicidin has been used as a histone deacetylase 2 (HDAC2) inhibitor to study its effects on 5-lipoxygenase (5-LO) mRNA expression in cell lines of Mono Mac6. It has also been used to study the effects of toll-like receptor 8 (TLR-8) stimulation and histone modification on the expression of an activator protein 1 [AP-1] family member(Fra-2) and tissue inhibitor of metalloproteinases 1 (TIMP-1) in monocytes.

Technology Process of methyl 6-[(3S,6S,9S,12R)-3-butan-2-yl-6-[(1-methoxyindol-3-yl)methyl]-2,5,8,11-tetraoxo-1,4,7,10-tetrazabicyclo[10.4.0]hexadecan-9-yl]hexanoate

There total 23 articles about methyl 6-[(3S,6S,9S,12R)-3-butan-2-yl-6-[(1-methoxyindol-3-yl)methyl]-2,5,8,11-tetraoxo-1,4,7,10-tetrazabicyclo[10.4.0]hexadecan-9-yl]hexanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

: 314058-15-6
(6S,9S,12S,14aR)-6-((S)-sec-Butyl)-12-(6-hydroxy-octyl)-9-(1-methoxy-1H-indol-3-ylmethyl)-decahydro-4a,7,10,13-tetraaza-benzocyclododecene-5,8,11,14-tetraone

: 183506-66-3
apicidin

Guidance literature:: With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In dichloromethane;
DOI:10.3987/com-00-9014

Reference yield:

: 147960-24-5
methyl (((9H-fluoren-9-yl)methoxy)carbonyl)-L-tryptophanate

: 183506-66-3
apicidin

Guidance literature:: Multi-step reaction with 11 steps

1.1: 83 percent / TFA

2.1: H₂O₂ / Na₂WO₄

2.2: 25 percent / NaHCO₃

3.1: 60 percent / Et₂NH

4.1: 63 percent / EDC; HOBt; N-ethylmorpholine

5.1: LiOH

6.1: 61 percent / EDC; HOBt; N-ethylmorpholine

7.1: LiOH

8.1: aq. HCl / acetic acid

9.1: pentafluorophenyl diphenylphosphinate; N-ethylmorpholine / dimethylformamide

10.1: TBAF; MS 4A / tetrahydrofuran / 24 h

11.1: 88 percent / TPAP; NMO; MS 4A / CH₂Cl₂

With N-ethylmorpholine;; hydrogenchloride; lithium hydroxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pentafluorophenyl diphenyl-phosphinate; tetrabutyl ammonium fluoride; dihydrogen peroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; trifluoroacetic acid; sodium tungstate; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.3987/com-00-9014

Reference yield:

: C₃₃H₃₈N₂O₄Si

: 183506-66-3
apicidin

Guidance literature:: Multi-step reaction with 10 steps

1.1: H₂O₂ / Na₂WO₄

1.2: 25 percent / NaHCO₃

2.1: 60 percent / Et₂NH

3.1: 63 percent / EDC; HOBt; N-ethylmorpholine

4.1: LiOH

5.1: 61 percent / EDC; HOBt; N-ethylmorpholine

6.1: LiOH

7.1: aq. HCl / acetic acid

8.1: pentafluorophenyl diphenylphosphinate; N-ethylmorpholine / dimethylformamide

9.1: TBAF; MS 4A / tetrahydrofuran / 24 h

10.1: 88 percent / TPAP; NMO; MS 4A / CH₂Cl₂

With N-ethylmorpholine;; hydrogenchloride; lithium hydroxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pentafluorophenyl diphenyl-phosphinate; tetrabutyl ammonium fluoride; dihydrogen peroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; diethylamine; sodium tungstate; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.3987/com-00-9014