4-(diphenylamino)butan-1-ol | 227805-94-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(diphenylamino)butan-1-ol
• 英文别名: 4-(N,N-diphenylamino)butanol；4-Diphenylamino-butan-1-ol；4-(N-phenylanilino)butan-1-ol
• CAS: 227805-94-9
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: KBDFRMKVRZJHHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(diphenylamino)butan-1-ol 在 六氯丙酮 、 sodium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N,N-diethyl-N',N'-diphenylbutane-1,4-diamine
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of New Chemosensitizers in Multi-Drug-Resistant Plasmodium falciparum

  摘要：

  A series of new chemosensitizers (modulators) against chloroquine-resistant Plasmodium falciparum were designed and synthesized in an attempt to fabricate modulators with enhancing drug-resistant reversing efficacy and minimal side effects. Four aromatic amine ring systems-phenothiazine, iminodibenzyl, iminostilbene, and diphenylamine-were examined. Various tertiary amino groups including either noncyclic or cyclic aliphatic amines were introduced to explore the steric tolerance at the end of the side chain. The new compounds showed better drug-resistant reversing activity in chloroquine-resistant than in mefloquine-resistant cell lines and were generally more effective against chloroquine-resistant P. falciparum isolates from Southeast Asian (W2 and TM91C235) than those from South America (PC49 and RCS). Structure-activity relationship studies revealed that elongation of the alkyl side chain of the molecule retained the chemosensitizing activity, and analogues with four-carbon side chains showed superior activity. Furthermore, new modulators with phenothiazine ring exhibited the best chemosensitizing activity among the four different ring systems examined. Terminal amino function has limited steric tolerance as evidenced by the dramatic lose of the modulating activity, when the size of substituent at the amino group increases. The best new modulator synthesized in this study possesses all three optimized structural features, which consist of a phenothiazine ring and a pyrrolidinyl group joined by a four-carbon alkyl bridge. The fractional inhibitory concentration TIC) index of the best compound is 0.21, which is superior to that of verapamil (0.51), one of the best-known multi-drug-resistant reversing agents. Some of the analogues displayed moderate intrinsic in vitro antimalarial activity against a W-2 clone of P. falciparum.

  DOI：

  10.1021/jm010549o
• 作为产物：
  描述：

  diphenyl[4-[(tetrahydropyran-2-yl)oxy]butyl]amine 在 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以78%的产率得到4-(diphenylamino)butan-1-ol
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of New Chemosensitizers in Multi-Drug-Resistant Plasmodium falciparum

  摘要：

  A series of new chemosensitizers (modulators) against chloroquine-resistant Plasmodium falciparum were designed and synthesized in an attempt to fabricate modulators with enhancing drug-resistant reversing efficacy and minimal side effects. Four aromatic amine ring systems-phenothiazine, iminodibenzyl, iminostilbene, and diphenylamine-were examined. Various tertiary amino groups including either noncyclic or cyclic aliphatic amines were introduced to explore the steric tolerance at the end of the side chain. The new compounds showed better drug-resistant reversing activity in chloroquine-resistant than in mefloquine-resistant cell lines and were generally more effective against chloroquine-resistant P. falciparum isolates from Southeast Asian (W2 and TM91C235) than those from South America (PC49 and RCS). Structure-activity relationship studies revealed that elongation of the alkyl side chain of the molecule retained the chemosensitizing activity, and analogues with four-carbon side chains showed superior activity. Furthermore, new modulators with phenothiazine ring exhibited the best chemosensitizing activity among the four different ring systems examined. Terminal amino function has limited steric tolerance as evidenced by the dramatic lose of the modulating activity, when the size of substituent at the amino group increases. The best new modulator synthesized in this study possesses all three optimized structural features, which consist of a phenothiazine ring and a pyrrolidinyl group joined by a four-carbon alkyl bridge. The fractional inhibitory concentration TIC) index of the best compound is 0.21, which is superior to that of verapamil (0.51), one of the best-known multi-drug-resistant reversing agents. Some of the analogues displayed moderate intrinsic in vitro antimalarial activity against a W-2 clone of P. falciparum.

  DOI：

  10.1021/jm010549o

文献信息

• Chemosensitizing agents against chloroquine resistant plasmodium falciparum and methods of making and using thereof
  申请人：——

  公开号：US20030032801A1

  公开（公告）日：2003-02-13

  A compound having the structural formula 1 or a pharmaceutically acceptable salt or prodrug thereof, wherein X is a substituted or unsubstituted alkyl or a heteroatom; n is 4, 5 or 6; Y is a substituted or unsubstituted alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, or 2 wherein R 1 and R 2 are each independently, H, a heteroatom, substituted or unsubstituted alkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; and wherein each ring structure are independently substituted or unsubstituted is disclosed. Also disclosed are chemosensitizing agents and methods of modulating, attenuating, reversing, or affecting a cell's or organism's resistance to a given drug such as an antimalarial.

  一种具有结构式1的化合物，或其药物可接受的盐或前药，其中X是取代或未取代的烷基或杂原子; n为4、5或6; Y是取代或未取代的烷基、环烷基、杂环烷基、芳基、杂芳基或2，其中R1和R2各自独立地为H、杂原子、取代或未取代的烷基、环烷基、杂环烷基、芳基或杂芳基;并且每个环结构都是独立取代或未取代的。还公开了化学增敏剂和调节、减弱、逆转或影响细胞或生物对给定药物（如抗疟药）的耐药性的方法。
• Omega-quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal antiinflammatory drugs
  申请人：SYNTEX PHARMACEUTICALS INTERNATIONAL LIMITED

  公开号：EP0289262A2

  公开（公告）日：1988-11-02

  Quaternary ammonium alkyl esters and thioesters of acidic nonsteroidal anti-inflammatory drugs (NSAIDs) are disclosed. These esters and thioesters display the anti-­inflammatory profile of the parent NSAIDs with greatly reduced gastrointestinal irritancy, providing a more favorable separation of therapeutic activity and toxicological side effects than the parent NSAIDs.

  本发明公开了酸性非甾体抗炎药（NSAIDs）的季铵烷基酯和硫代酯。这些酯类和硫代酯类具有母体非甾体抗炎药的抗炎特性，但胃肠道刺激性大大降低，与母体非甾体抗炎药相比，能更有效地将治疗活性和毒副作用分开。
• AQUEOUS SILYLATED URETHANE COMPOSITION, AQUEOUS ADHESIVES FOR WRAPPING, AND AQUEOUS CONTACT ADHESIVES
  申请人：KONISHI CO., LTD.

  公开号：EP1607423A1

  公开（公告）日：2005-12-21

  A water-based silylated urethane composition is used as a water-based adhesive that has high safety, develops satisfactory tackiness in a short time and has excellent initial bond strength. The water-based silylated urethane composition contains following Components (A), (B) and (C): (A) a urethane prepolymer containing an anionic group and a tertiary amino group and having a terminal alkoxysilyl group, the urethane prepolymer (A) being a reaction product of an anionic-group-free polyol compound (A1), an anionic-group-containing polyol compound (A2), a compound (A3) containing a tertiary amino group and an isocyanate-reactive group, a polyisocyanate compound (A4), an alkoxysilane compound (A5) containing an isocyanate-reactive group, and an amine-based chain extender (A6); (B) a basic compound; and (C) water

  一种水基硅烷化聚氨酯组合物可用作水基粘合剂，它具有很高的安全性，能在短时间内产生令人满意的粘性，并具有出色的初始粘合强度。水基硅烷化聚氨酯组合物包含以下成分（A）、（B）和（C）： (A) 含有阴离子基团和叔氨基且具有末端烷氧基硅烷基团的聚氨酯预聚物，聚氨酯预聚物 (A) 是不含阴离子基团的多元醇化合物 (A1)、含阴离子基团的多元醇化合物 (A2) 的反应产物、一种含有叔氨基和异氰酸酯反应基团的化合物 (A3)、一种多异氰酸酯化合物 (A4)、一种含有异氰酸酯反应基团的烷氧基硅烷化合物 (A5) 和一种胺基扩链剂 (A6)； (B) 碱性化合物；以及 (C) 水
• Aqueous silylated urethane compositions, aqueous adhesives for wrapping, and aqueous contact adhesives
  申请人：Harada Kuniharu

  公开号：US20060183845A1

  公开（公告）日：2006-08-17

  A water-based silylated urethane composition is used as a water-based adhesive that has high safety, develops satisfactory tackiness in a short time and has excellent initial bond strength. The water-based silylated urethane composition contains following Components (A), (B) and (C): (A) a urethane prepolymer containing an anionic group and a tertiary amino group and having a terminal alkoxysilyl group, the urethane prepolymer (A) being a reaction product of an anionic-group-free polyol compound (A1), an anionic-group-containing polyol compound (A2), a compound (A3) containing a tertiary amino group and an isocyanate-reactive group, a polyisocyanate compound (A4), an alkoxysilane compound (A5) containing an isocyanate-reactive group, and an amine-based chain extender (A6); (B) a basic compound; and (C) water

  一种水基硅烷化聚氨酯组合物可用作水基粘合剂，它具有很高的安全性，能在短时间内产生令人满意的粘性，并具有出色的初始粘合强度。水基硅烷化聚氨酯组合物包含以下成分（A）、（B）和（C）：(A) 含有阴离子基团和叔氨基且具有末端烷氧基硅烷基团的聚氨酯预聚物，聚氨酯预聚物 (A) 是不含阴离子基团的多元醇化合物 (A1)、含阴离子基团的多元醇化合物 (A2) 的反应产物、一种含有叔氨基和异氰酸酯反应基团的化合物 (A3)、一种多异氰酸酯化合物 (A4)、一种含有异氰酸酯反应基团的烷氧基硅烷化合物 (A5) 和一种胺基扩链剂 (A6)；(B) 碱性化合物；以及 (C) 水
• JPS5484578A
  申请人：——

  公开号：JPS5484578A

  公开（公告）日：1979-07-05