3-(2-carboxy-ethyl)-14-ethyl-13-formyl-4,8,18-trimethyl-20-oxo-9-vinyl-23H,25H-phorbine-21-carboxylic acid methyl ester | 20239-99-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 3-(2-carboxy-ethyl)-14-ethyl-13-formyl-4,8,18-trimethyl-20-oxo-9-vinyl-23H,25H-phorbine-21-carboxylic acid methyl ester
• 英文别名: pheophorbide b；3-(2-carboxy-ethyl)-14-ethyl-13-formyl-4,8,18-trimethyl-20-oxo-9-vinyl-23H,25H-phorbine-21-carboxylic acid methyl ester；Pheophorbid-b；pheophorbide-b；Phaeophorbid-b；(3S-(3α,4β,21β))-14-ethyl-13-formyl-21-(methoxycarbonyl)-4,8,18-trimethyl-20-oxo-9-vinylphorbine-3-propionic acid
• CAS: 20239-99-0；92935-95-0
• 化学式: C₃₅H₃₄N₄O₆
• 分子量: 606.678
• InChiKey: PROPHBCDMQAJMH-HSJXTSEBSA-N

物化性质

• 沸点：
  1085.6±65.0 °C(Predicted)
• 密度：
  1.351±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  45.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  155.1
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-(2-carboxy-ethyl)-14-ethyl-13-formyl-4,8,18-trimethyl-20-oxo-9-vinyl-23H,25H-phorbine-21-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 1H-benzotriazol-1-yl methanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 bis(pheophorbide b)ethylene glycol diester
  参考文献：
  名称：

  Synthesis of covalently linked dimeric derivatives of chlorophyll a, pyrochlorophyll a, chlorophyll b, and bacteriochlorophyll a

  摘要：

  DOI：

  10.1021/jo01298a043
• 作为产物：
  描述：

  pheophytin b 以 水 、 三氟乙酸 为溶剂， 以93%的产率得到3-(2-carboxy-ethyl)-14-ethyl-13-formyl-4,8,18-trimethyl-20-oxo-9-vinyl-23H,25H-phorbine-21-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of covalently linked dimeric derivatives of chlorophyll a, pyrochlorophyll a, chlorophyll b, and bacteriochlorophyll a

  摘要：

  DOI：

  10.1021/jo01298a043

文献信息

• Water-soluble porphyrin derivatives for photodynamic therapy, their use and manufacture
  申请人：CeramOptec Industries Inc.

  公开号：US20030023081A1

  公开（公告）日：2003-01-30

  High purity pharmaceutical-grade water-soluble porphyrin derivatives having a general formula given by formula 1 or 2 and new methods to prepare and use such porphyrin derivatives: 1 Wherein B is a ring having the structure: 2 Wherein: R 1 ═—CH═CH 2 , —CH(OAlk)CH 3 , —CHO, —C(O)CH 3 , —CH 2 CH 3 , —CH(Alk)CH(COAlk) 2 , —CH 2 CH(COAlk) 2 , —CH(Alk)CH 2 COAlk, —CH(Alk)CH 2 CH(OH)CH 3 , and —CH 2 CH 2 CH(OH)CH 3 R 2 ═—CH 3 , —CHO, —CH(OH)Alk, —CH═CHAlk, CH 2 OH, and CH 2 OAlk; R 3 ═—OH, —OAlk, —NH-Alk, NH—X—COO − (HG) + , —NH—Y—NR 8 R 9 , -and NH—Y—OH; R 4 ═—OAlk, —NH-Alk, and NH—X—COO − (HG) + ; R 5 ═—OAlk, —NH-Alk, and NH—X—COO − (HG) + ; R 6 ═H and —COOAlk; R 7 ═—O − (HG) + , —OAlk, —NH-Alk, and —NH—X—COO − (HG) + ; R 8 ═H and Alk R 9 ═H and Alk Wherein: —NH—X—COO − =the residue of organic amino acid; X=alkylidene, peptides, oligopeptides and —(CH 2 CH 2 O) n CH 2 CH 2 —, wherein n= 1 - 30; Y=alkylidene and —(CH 2 CH 2 O) n CH 2 CH 2 —, wherein n= 1 - 30; G=a hydrophilic organic amine (fex. N-methyl-D-glucamine and other amino-group containing carbohydrate derivatives, TRIS, amino acids, oligopeptides); and Alk=an alkyl substituent. An embodiment of the present invention consists of a method to prepare water-soluble porphyrin derivatives comprising the steps of one- or two-step direct acidic alcoholysis of biological raw material producing a crystalline alkyl pheophorbide, conversion of the obtained alkyl pheophorbide into an acidic porphyrin, and reaction of the acidic porphyrin in water or in an aqueous organic solution with a hydrophilic organic amine. Another embodiment of the present invention consists of a method to prepare water-soluble porphyrin derivatives, comprising reaction of acidic porphyrins prepared by any known method in water or in aqueous organic solution with a hydrophilic organic amine. Another embodiment of the present invention comprises the additional step of purification of the resultant water-soluble porphyrin derivative by reversed phase chromatography using volatile solvents. The compound disclosed in the present invention can be used as photosensitizers for the photodynamic therapy of cancer, infectious and other diseases as well as for light irradiation treatments in other cases.

  具有通式1或2给出的一般式的高纯度制药级水溶性卟啉衍生物，以及制备和使用此类卟啉衍生物的新方法： 其中B是具有以下结构的环： 其中： R1为— 、—CH(OAlk)CH3、—CHO、—C(O) 、— 、—CH(Alk)CH(COAlk)2、— CH(COAlk)2、—CH(Alk) COAlk、—CH(Alk) CH(OH) 和— CH(OH) ； R2为— 、—CHO、—CH(OH)Alk、—CH2CHAlk、 OH和 OAlk； R3为—OH、—OAlk、—NH-Alk、NH—X—COO−(HG)、—NH—Y—NR8R9和NH—Y—OH； R4为—OAlk、—NH-Alk和NH—X—COO−(HG)； R5为—OAlk、—NH-Alk和NH—X—COO−(HG)； R6为H和—COOAlk； R7为—O−(HG)、—OAlk、—NH-Alk和—NH—X—COO−(HG)； R8为H和Alk； R9为H和Alk； 其中： —NH—X—COO−为有机氨基酸的残基； X为烷基亚甲基、肽、寡肽和—( O)n —，其中n=1-30； Y为烷基亚甲基和—( O)n —，其中n=1-30； G为亲水性有机胺（例如N-甲基-D-葡萄糖胺和其他含氨基糖衍生物、TRIS、氨基酸、寡肽）； Alk为烷基取代基。 本发明实施例包括一种制备水溶性卟啉衍生物的方法，包括以下步骤：通过一步或两步直接酸性醇解生物原料产生结晶烷基叶绿素，将获得的烷基叶绿素转化为酸性卟啉，将酸性卟啉在水或水有机溶液中与亲水性有机胺反应。本发明的另一实施例包括一种制备水溶性卟啉衍生物的方法，包括将通过任何已知方法制备的酸性卟啉在水或水有机溶液中与亲水性有机胺反应。本发明的另一实施例包括通过使用挥发性溶剂进行反相色谱纯化的额外步骤来净化所得的水溶性卟啉衍生物。本发明中披露的化合物可用作癌症、传染性疾病和其他疾病的光动力疗法的光敏剂，以及用于其他情况下的光照治疗。
• Water-soluble porphyrin derivatives and methods of their preparation
  申请人：CeramOptec Industries, Inc.

  公开号：US20030004334A1

  公开（公告）日：2003-01-02

  The invention relates to the chemistry of biologically active compounds, namely, to a new method to prepare water-soluble porphyrin derivatives, particularly chlorin derivatives having general formulae (1). The compounds of the present invention are useful as photosensitizers for the photodynamic therapy of cancer, of infectious and other diseases, as well as for light irradiation treatments in other cases. 1 where: R 1 ═—CH═CH 2 , —CH(OAlk)CH 3 , —CHO, —C(O)CH 3 ; —CH 2 CH 3 ; —CH(Alk)CH(COAlk) 2 , —CH 2 CH(COAlk) 2 , —CH(Alk)CH 2 COAlk, —CH(Alk)CH 2 CH(OH)CH 3 , —CH 2 CH 2 CH(OH)CH 3 R 2 ═—CH 3 , —CHO, —CH(OH)Alk, —CH═CHAlk, CH 2 OH, CH 2 OAlk; R 3 ═H or lower allyl; G=hydrophilic organic amine (f. ex. N-methyl-D-glucamine and other amino-group containing carbohydrate derivatives, TRIS, aminoacids, oligopeptides). Alk=alkyl substituent.

  本发明涉及生物活性化合物的化学，特别是一种制备水溶性卟啉衍生物的新方法，尤其是具有一般式（1）的叶绿素衍生物。本发明的化合物可用作光敏剂，用于癌症、传染病和其他疾病的光动力疗法，以及其他情况下的光照射治疗。其中：R1 = H-CH2- ，-CH（OAlk）CH3，-CHO，-C（O） ；- ；-CH（Alk）CH（COAlk）2，- CH（COAlk）2，-CH（Alk） COAlk，-CH（Alk） CH（OH） ，- CH（OH） ；R2 = - ，-CHO，-CH（OH）Alk，-CH=CHAlk， OH， OAlk；R3 = H或较低的烯丙基；G = 亲水性有机胺（例如N-甲基-D-葡萄糖胺和其他含氨基的碳水化合物衍生物、TRIS、氨基酸、寡肽）。Alk = 烷基取代基。
• Chlorin photosensitizing agents for use in photodynamic therapy
  申请人：Robinson C Byron

  公开号：US20050020559A1

  公开（公告）日：2005-01-27

  Chlorin compounds and compositions useful in photodynamic therapy for treating ophtalmic, cardiovascular, skin, and cancer or malignant diseases.

  氯素化合物和组合物在光动力疗法中用于治疗眼科、心血管、皮肤、癌症或恶性疾病。
• Porphyric insecticides
  申请人：The Board of Trustees for the University of Illinois

  公开号：EP0326835A1

  公开（公告）日：1989-08-09

  Insecticidal compositions comprising one or more compounds' selected from the group consisting of delta-aminolevulinic acid, inducers of delta aminolevulinic acid, and enhancers of delta-aminolevulinic acid conversion to photodynamic tetrapyrroles; and methods of making and using same.

  包含一种或多种选自δ-氨基乙酰丙酸、δ-氨基乙酰丙酸诱导剂和δ-氨基乙酰丙酸转化为光动力四吡咯的增强剂的化合物的杀虫组合物；以及其制造和使用方法。
• Dye-sensitized solar cells and methods of making same
  申请人：Honeywell Romania S.R.L.

  公开号：EP2730622A1

  公开（公告）日：2014-05-14

  The present disclosure relates to dye-sensitized solar cells (DSSC) comprising a tetrapyrrole macrocycle and methods of making such DSSCs.

  本公开涉及包含四吡咯大环的染料敏化太阳能电池（DSSC）以及制造这种 DSSC 的方法。