4-メトキシ-5-(4-ペンチル-5-メチル-2H-ピロール-2-イリデンメチル)-2,2'-ビ[1H-ピロール]

4-メトキシ-5-(4-ペンチル-5-メチル-2H-ピロール-2-イリデンメチル)-2,2'-ビ[1H-ピロール] 化学構造式
82-89-3
CAS番号.
82-89-3
化学名:
4-メトキシ-5-(4-ペンチル-5-メチル-2H-ピロール-2-イリデンメチル)-2,2'-ビ[1H-ピロール]
别名:
3-メトキシ-2-(5-メチル-4-ペンチル-2H-ピロール-2-イリデン)メチル-5-(1H-ピロール-2-イル)-1H-ピロール;4-メトキシ-5-(4-ペンチル-5-メチル-2H-ピロール-2-イリデンメチル)-2,2'-ビ[1H-ピロール];プロジギオシン;4-メトキシ-5-[(5-メチル-4-ペンチル-2H-ピロール-2-イリデン)メチル]-2,2'-ビ[1H-ピロール];4-メトキシ-5-[(5-メチル-4-ペンチル-2H-ピロール-2-イリデン)メチル]-1H,1'H-2,2'-ビピロール;4-メトキシ-5-[(5-メチル-4-ペンチル-2H-ピロール-2-イリデン)メチル]-2,2′-ビ[1H-ピロール];4-メトキシ-5-(4-ペンチル-5-メチル-2H-ピロール-2-イリデンメチル)-2,2′-ビ[1H-ピロール];4-メトキシ-5-(4-ペンチル-5-メチル-2H-ピロール-2-イリデンメチル)-2,2′-ビ(1H-ピロール)
英語名:
PRODIGIOSIN
英語别名:
Nsc47147;Aids010622;Aids-010622;PRODIGIOSIN;Prodigiosine;Prodigiosin, apoptotic agent;2-Methyl-3-amyl-6-methoxyprodigiosene;Prodigiosin Serratia marcescens;4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl], 2,2'bipyrrole;4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2'-bi[1H-pyrrol]
CBNumber:
CB5156304
化学式:
C20H25N3O
分子量:
323.43
MOL File:
82-89-3.mol
MSDS File:
SDS

4-メトキシ-5-(4-ペンチル-5-メチル-2H-ピロール-2-イリデンメチル)-2,2'-ビ[1H-ピロール] 物理性質

融点 :
151-152°
沸点 :
554.3±50.0 °C(Predicted)
比重(密度) :
1.12±0.1 g/cm3(Predicted)
貯蔵温度 :
-20C
溶解性:
Acetonitrile: Soluble; Ethanol: Soluble; Methanol: Soluble
外見 :
暗赤色の固体
酸解離定数(Pka):
17.09±0.50(Predicted)
色:
Dark red
InChI:
InChI=1S/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,21,23H,4-6,8H2,1-3H3
InChIKey:
SZXDNGVQRDTJSD-UHFFFAOYSA-N
SMILES:
N1C(C=C2C=C(CCCCC)C(C)=N2)=C(OC)C=C1C1=CC=CN1

安全性情報

4-メトキシ-5-(4-ペンチル-5-メチル-2H-ピロール-2-イリデンメチル)-2,2'-ビ[1H-ピロール] 価格

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入

4-メトキシ-5-(4-ペンチル-5-メチル-2H-ピロール-2-イリデンメチル)-2,2'-ビ[1H-ピロール] 化学特性,用途語,生産方法

使用

Prodigiosin is an intensely red, pyrrole pigment produced by several bacteria, most notably Serratia marcescens. Prodigiosin has a broad biological profile with activity against fungi, tumour cell lines and malaria. It was shown to be an immunosuppressant in 2007. Prodigiosin acts via caspase inhibition to induce of apoptosis in human primary cancer cells. Prodigiosin also acts as an inducer of p21WAF1/CIP1 expression via transforming growth factor-β receptor pathway, and activates NAG-1 via glycogen synthase kinase-3β.

定義

ChEBI: A member of the class of tripyrroles that is a red-coloured pigment with antibiotic properties produced by Serratia marcescens.

一般的な説明

A cell-permeable tripyrrole alkaloid compound that displays immunosuppressive and anti-tumor properties irrespective of p53 status and multidrug resistance. Shown to selectively upregulate p21WAF/CIP1 and NAG-1 (nonsteroidal anti-inflammatory drug-activated gene 1) and downregulate survivin expression levels, induce mitochondria-mediated apoptosis and cell cycle arrest in tumor cells. Prevents FADD phosphorylation (IC50 = 2.0 μM in A549-FKR cells) through inhibition of FADD-kinase CK1α (IC50 ~ 6.0 μM in SW620-BGCR cells) and augments cisplatin (Cat. No. 232120)-induced apoptosis. Blocks NF-κB activation by decreasing pIκBα (by 63% at 3 μM) and IκBα levels in A549 cells, and shrinks tumor growth in A549-FKR tumor xenograft mouse model (3 mg/kg, i.p., o.d.).

酵素阻害剤

This red bacterial pigment (FWfree-base = 323.44 g/mol; melting point = 151- 152°C) is an antibiotic produced by Serratia marcescens (formerly Chromobacterium prodigiosum). Prodigiosin is the parent member of a class of pyrrole-containing natural products that exhibit immunosuppressive, cytotoxic, and apoptotic activity and can facilitate copper-promoted oxidative double-strand DNA cleavage through reductive activation of Cu2+. They also uncouple lysosomal vacuolar-type ATPases by promoting H+/Cl– symport activity. The solid pigment is dark red and displays a green reflex. Acidic aqueous solutions are also red, but neutral or alkaline solutions are orange-yellow. Target(s): DNA topoisomerase I; DNA topoisomerase II; FoF1 ATPase, or H+-transporting two-sector ATPase, as an uncoupler; H+/K+-ATPase, as an uncoupler; proton translocation, as an uncoupler; and Serratia marcescens nuclease.

4-メトキシ-5-(4-ペンチル-5-メチル-2H-ピロール-2-イリデンメチル)-2,2'-ビ[1H-ピロール] 上流と下流の製品情報

原材料

準備製品


4-メトキシ-5-(4-ペンチル-5-メチル-2H-ピロール-2-イリデンメチル)-2,2'-ビ[1H-ピロール] 生産企業

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82-89-3(4-メトキシ-5-(4-ペンチル-5-メチル-2H-ピロール-2-イリデンメチル)-2,2'-ビ[1H-ピロール])キーワード:


  • 82-89-3
  • PRODIGIOSIN
  • (Z)-4-Methoxy-5-((5-Methyl-4-pentyl-2H-pyrrol-2-ylidene)Methyl)-1H,1'H-2,2'-bipyrrole
  • 3-Methoxy-2-(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl-5-(1H-pyrrol-2-yl)-1H-pyrrole
  • 4-Methoxy-5-(4-pentyl-5-methyl-2H-pyrrole-2-ylidenemethyl)-2,2'-bi[1H-pyrrole]
  • 4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2'-bi[1H-pyrrol]
  • 4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2'-bi[1H-pyrrole]
  • Prodigiosine
  • 4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl], 2,2'bipyrrole
  • Aids010622
  • Aids-010622
  • Nsc47147
  • 2,2'-Bi-1H-pyrrole,4-Methoxy-5-[(5-Methyl-4-pentyl-2H-pyrrol-2-ylidene)Methyl]-prodigiosinⅡ≤
  • 2,2'-Bi-1H-pyrrole,4-Methoxy-5-[(5-Methyl-4-pentyl-2H-pyrrol-2-ylidene)Methyl]-
  • 2-Methyl-3-amyl-6-methoxyprodigiosene
  • (E)-4-methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)-1H,1'H-2,2'-bipyrrole
  • Prodigiosin, apoptotic agent
  • Prodigiosin Serratia marcescens
  • 4-Methoxy-5-((5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl)-1H,1'H-2,2'-bipyrrole
  • 3-メトキシ-2-(5-メチル-4-ペンチル-2H-ピロール-2-イリデン)メチル-5-(1H-ピロール-2-イル)-1H-ピロール
  • 4-メトキシ-5-(4-ペンチル-5-メチル-2H-ピロール-2-イリデンメチル)-2,2'-ビ[1H-ピロール]
  • プロジギオシン
  • 4-メトキシ-5-[(5-メチル-4-ペンチル-2H-ピロール-2-イリデン)メチル]-2,2'-ビ[1H-ピロール]
  • 4-メトキシ-5-[(5-メチル-4-ペンチル-2H-ピロール-2-イリデン)メチル]-1H,1'H-2,2'-ビピロール
  • 4-メトキシ-5-[(5-メチル-4-ペンチル-2H-ピロール-2-イリデン)メチル]-2,2′-ビ[1H-ピロール]
  • 4-メトキシ-5-(4-ペンチル-5-メチル-2H-ピロール-2-イリデンメチル)-2,2′-ビ[1H-ピロール]
  • 4-メトキシ-5-(4-ペンチル-5-メチル-2H-ピロール-2-イリデンメチル)-2,2′-ビ(1H-ピロール)
  • 抗生物質
  • 抗真菌薬
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