2-bromo-4-(4-carboxyphenyl)butanal | 80577-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-4-(4-carboxyphenyl)butanal
• 英文别名: Benzoic acid, 4-(3-bromo-4-oxobutyl)-；4-(3-bromo-4-oxobutyl)benzoic acid
• CAS: 80577-69-1
• 化学式: C₁₁H₁₁BrO₃
• 分子量: 271.111
• InChiKey: AJKMNRHUDYEIFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-4-(4-carboxyphenyl)butanal 在 sodium hydroxide 、 potassium triiodide 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 乙二醇甲醚 为溶剂， 反应 29.5h， 生成 10-去氮杂氨基蝶呤
  参考文献：
  名称：

  10-烷基-10-去氮杂蝶呤的合成和抗肿瘤活性。一种方便的10-脱氮蝶呤合成方法。

  摘要：

  大规模合成有效的抗肿瘤药10-脱氮蝶呤的要求导致了该化合物及其10-烷基类似物的简便合成的发展。用3-甲氧基烯丙基氯将适当的对烷基苯甲酸的二异丙基氨基锂锂生成的二价阴离子烷基化。在pH 7-8下将所得的4-（对羧基苯基）-1-甲氧基-1-丁烯溴化，得到2-溴-4-（对羧基苯基）丁醛。与2,4,5,6-四氨基嘧啶缩合，然后原位氧化所得的二蝶啶，得到结晶的10-烷基-10-脱氮基-4-氨基-4-脱氧蝶酸。通过混合酸酐法将蝶酸与谷氨酸二乙酯偶联，然后在室温下皂化，以得到目标10-脱氮蝶呤类化合物。10-烷基化合物作为叶酸依赖性细菌的生长抑制剂与10-脱氮蝶呤大致相等。它们抑制干酪乳杆菌和L1210衍生的二氢叶酸还原酶的能力也相似。体外转运特性提示10-烷基类似物的治疗指数得到改善。相对于小鼠中的L1210，在LD10剂量下，寿命延长百分比为+ 151％（甲氨蝶呤），+ 178％（10-脱氮蝶呤），+

  DOI：

  10.1021/jm00352a026
• 作为产物：
  描述：

  4-((E)-4-Methoxy-but-3-enyl)-benzoic acid 在 溴 、 碳酸氢钠 、 盐酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-bromo-4-(4-carboxyphenyl)butanal
  参考文献：
  名称：

  Analogues of the Potent Nonpolyglutamatable Antifolate N^α-(4-Amino-4-deoxypteroyl)-N^δ-hemiphthaloyl-l-ornithine (PT523) with Modifications in the Side Chain, p-Aminobenzoyl Moiety, or 9,10-Bridge:  Synthesis and in Vitro Antitumor Activity

  摘要：

  Seven N-alpha-(4-amino-4-deoxypteroyl)-N-sigma-hemiphtha (2, PT523) analogues were synthesized by modifications of the literature synthesis of the corresponding AMT (1) analogues and were tested as inhibitors of tumor cell growth. in growth assays against cultured CCRF-CEM human leukemic cells exposed to drug for 72 h, the IC50 values of analogues in which N-10 was replaced by CH2 and CHMe were found to be 0.55 +/- 0.07 and 0.63 +/- 0.08 nM, and thus these analogues are more potent than 1 (IC50 = 4.4 +/- 1.0 nM) or 2 (IC50 = 1.5 +/-: 0.39 nM). The 10-ethyl-10-deaza analogue of 2 (IC50 = 1.2 +/- 0.25 nM) was not statistically different from 2 but was more potent than edatrexate, the 10-ethyl-10-deaza analogue of 1, which had an IC50 of 3.3 +/- 0.36 nM. In contrast, the analogue of 2 with both an ethyl and a CO2Me group at the 10-position had an IC50 of 54 +/- 4.9 nM, showing this modification to be unfavorable. The 4-amino-1-naphthoic acid analogue of 2 had an IC50 Of 1.2 +/- 0.22 nM, indicating that replacement of the p-aminobenzoic acid (pABA) moiety does not diminish cytotoxicity. The analogues in which the (CH2)(3) Side chain was replaced by slightly longer CH2SCH2 and (CH2)(2)-SCH2 groups gave IC50 values of 4.4 +/- 1.1 and 5.0 +/- 0.56 nM and thus were somewhat less potent than the parent molecule. However the analogues in which the aromatic COOH group was at the meta and para positions of the phthaloyl ring had IC50 values of 7.5 +/- 0.47 and 55 +/- 0.07 nM, confirming the low potency we had previously observed with these compounds against other cell lines. Overall, the results in this study support the conclusion that, while the position of the phthaloyl COOH group and the length of the amino acid side chain in 2 are important determinants of cytotoxic potency, changes in the pABA region and 9,10-bridge are well-tolerated and can even increase potency.

  DOI：

  10.1021/jm990630f

文献信息

• [EN] PROCESS FOR THE PREPARATION OF PEMETREXED AND LYSIN SALT THEREOF<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE PÉMÉTREXED ET DU SEL DE LYSINE DE CELUI-CI
  申请人：BERLIN CHEMIE AG

  公开号：WO2014024164A1

  公开（公告）日：2014-02-13

  The present invention refers to a process for the synthesis of pemetrexed and salts thereof, in particular to a lysine salt thereof, to said salt as such and to pharmaceutical compositions that comprise the same. Furthermore, the present disclosure also relates to a crystalline form of the synthesis intermediate pemetrexed diethyl ether and a crystalline form of the pemetrexed lysine salt.

  本发明涉及一种合成培美曲塞及其盐的方法，特别是其赖氨酸盐，以及包含该盐的药物组合物。此外，本公开还涉及合成中间体培美曲塞二乙醚的结晶形式和培美曲塞赖氨酸盐的结晶形式。
• ORGANIC ELECTROLUMINESCENCE DEVICE, NOVEL PLATINUM COMPLEX COMPOUND AND NOVEL COMPOUND CAPABLE OF BEING A LIGAND THEREOF
  申请人：Murakami Takeshi

  公开号：US20090261721A1

  公开（公告）日：2009-10-22

  An organic electroluminescence device, includes: a pair of electrodes; and at least one organic layer including a light emitting layer, the light emitting layer being provided between the pair of electrodes, wherein at least one layer of the at least one organic layer contains a compound represented by formula (1) as defined in the specification.

  一种有机电致发光装置，包括：一对电极；以及至少一层有机层，包括发光层，所述发光层位于电极对之间，其中，所述至少一层有机层中至少含有一种由式（1）所表示的化合物，该式在说明书中有定义。
• STURTZ, GEORGES;VOISIN-DACHEUX, PATRICIA;GUILLAMOT, GERARD, C. R. ACAD. SCI. SER. 2, 310,(1990) N, C. 739-742
  作者：STURTZ, GEORGES、VOISIN-DACHEUX, PATRICIA、GUILLAMOT, GERARD

  DOI：——

  日期：——
• DEGRAW, J. I.;BROWN, V. H.;TAGAWA, H.;KISLIUK, R. L.;GAUMONT, Y.;SIROTNAK+, J. MED. CHEM., 1982, 25, N 10, 1227-1230
  作者：DEGRAW, J. I.、BROWN, V. H.、TAGAWA, H.、KISLIUK, R. L.、GAUMONT, Y.、SIROTNAK+

  DOI：——

  日期：——
• DEGRAW, J. I. ,, JR
  作者：DEGRAW, J. I. ,, JR

  DOI：——

  日期：——