prodigiosene | 22187-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: prodigiosene
• 英文别名: 2-(1H-pyrrol-2-yl)-5-[(Z)-pyrrol-2-ylidenemethyl]-1H-pyrrole
• CAS: 22187-69-5
• 化学式: C₁₃H₁₁N₃
• 分子量: 209.25
• InChiKey: PRPQBJVECMKSEO-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(methoxycarbonyl)-1,1'-carbonyldipyrrole 在 吡啶 、 polymer bound palladium acetate (2.79percent Pd) 、 lithium methanolate 、 氢溴酸 、 sodium carbonate 、 肼 作用下， 以 甲醇 、 乙二醇 、 溶剂黄146 为溶剂， 反应 40.99h， 生成 prodigiosene
  参考文献：
  名称：

  Total synthesis of prodigiosin, prodigiosene, and desmethoxyprodigiosin: Diels-Alder reactions of heterocyclic azadienes and development of an effective palladium(II)-promoted 2,2'-bipyrrole coupling procedure

  摘要：

  DOI：

  10.1021/jo00242a013

文献信息

• 2,2'-bi-1H-pyrrole derivatives with immunosuppressant activity
  申请人：Pharmacia Italia S.p.A.

  公开号：EP1241162A1

  公开（公告）日：2002-09-18

  New and known 5-[(2H-pyrrol-2-ylidene)methyl]-2,2'-bi-1H-pyrrole derivatives, having immunomodulating activity and, represented by the following general formula (I) wherein, subject to a proviso, R1 represents hydrogen, phenyl, C1-C20 alkyl or C2-C20 alkenyl, wherein the alkyl and alkenyl groups may be unsubstituted or substituted by 1 to 3 substituents chosen independently from halogen, C1-C6 alkoxy, hydroxy, aryl and aryloxy; R2 represents hydrogen, C1-C6 alkyl, cyano, carboxy or (C1-C6 alkoxy) carbonyl; R3 represents halogen, hydroxy or C1-C11 alkoxy unsubstituted or substituted by phenyl; R4 represent hydrogen, C1-C6 alkyl or phenyl; each or R5 and R6 independently represents hydrogen, C2-C20 alkanoyl, C3-C20 alkenoyl, phenyl, C1-C20 alkyl or C2-C20 alkenyl, wherein the alkanoyl, alkenoyl, alkyl and the alkenyl groups may be unsubstituted or substituted by 1 to 3 substituents chosen independently from halogen, C1-C6 alkoxy, hydroxy, aryl, aryloxy, cyano, carboxy, (C1-C6 alkoxy)carbonyl, (C3-C4 alkenyl)carbamoyl, aralkylcarbamoyl, arylcarbamoyl and -CONRcRd in which each of Rc and Rd independently is hydrogen or C1-C6 alkyl or Rc arid Rd, taken together with the nitrogen atom to which they are linked, form a morpholino or piperidino ring; or two of R4, R5 and R6 taken together form a C4-C12 polymethylene chain, which can be unsubstituted or substituted by a C1-C12 alkyl, by a C2-C12 alkenyl or by a C1-C12 alkylidene group, wherein the alkyl, alkenyl and alkylidene groups may be in turn unsubstituted or substituted by a substituent chosen from halogen, C1-C6 alkoxy, hydroxy, cyano, carboxy, (C1-C6 alkoxy)carbonyl, aryloxy and aryl; the remaining one being hydrogen or C1-C12 alkyl; and the pharmaceutically acceptable salts thereof, are disclosed.

  具有免疫调节活性的新的和已知的 5-[(2H-吡咯-2-亚基)甲基]-2,2'-双-1H-吡咯衍生物，由以下通式(I)表示 其中，根据但书，R1 代表氢、苯基、C1-C20 烷基或 C2-C20 烯基，其中烷基和烯基可以未被取代或被 1 至 3 个独立选自卤素、C1-C6 烷氧基、羟基、芳基和芳氧基的取代基取代；R2 代表氢、C1-C6 烷基、氰基、羧基或（C1-C6 烷氧基）羰基；R3 代表卤素、羟基或未被取代或被苯基取代的 C1-C11 烷氧基；R4 代表氢、C1-C6 烷基或苯基；其中每个 Rc 和 Rd 独立地为氢或 C1-C6 烷基，或 Rc 和 Rd 与它们连接的氮原子一起形成吗啉环或哌啶环；或 R4、R5 和 R6 中的两个共同形成 C4-C12 聚亚甲基链，该链可以未被 C1-C12 烷基、C2-C12 烯基或 C1-C12 亚烷基取代，其中烷基、烯基和亚烷基可依次未被取代或被选自卤素、C1-C6 烷氧基、羟基、氰基、羧基、(C1-C6 烷氧基)羰基、芳氧基和芳基的取代基取代；余下的一个为氢或 C1-C12 烷基；及其药学上可接受的盐，均已公开。
• NOVEL 2,2'-BI-1H-PYRROLE DERIVATIVES WITH IMMUNOSUPPRESSANT ACTIVITY
  申请人：Pharmacia S.p.A.

  公开号：EP0686147A1

  公开（公告）日：1995-12-13
• PROCESS FOR THE PREPARATION OF 2,2'-BIPYRROLYL-PYRROMETHENE (PRODIGIOSINS) DERIVATIVES
  申请人：PHARMACIA & UPJOHN S.p.A.

  公开号：EP0825983A1

  公开（公告）日：1998-03-04
• US5691334A
  申请人：——

  公开号：US5691334A

  公开（公告）日：1997-11-25
• US5847127A
  申请人：——

  公开号：US5847127A

  公开（公告）日：1998-12-08