2-bromo-4,6-dichlorobenzyl alcohol | 115615-21-9

• 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-4,6-dichlorobenzyl alcohol
• 英文别名: (2-Bromo-4,6-dichlorophenyl)methanol
• CAS: 115615-21-9
• 化学式: C₇H₅BrCl₂O
• 分子量: 255.926
• InChiKey: KKRGKPLATYTQGP-UHFFFAOYSA-N

物化性质

• 熔点：
  111-112 °C
• 沸点：
  319.8±37.0 °C(Predicted)
• 密度：
  1.785±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-bromo-4,6-dichlorobenzyl alcohol 在 正丁基锂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.33h， 生成 1-(3,5-DICHLORO-2-HYDROXYMETHYLPHENYL)-1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YL)ETHANOL
  参考文献：
  名称：

  Isobenzofurans as conformationally constrained miconazole analogs with improved antifungal potency

  摘要：

  A series of halogen-substituted isobenzofuran analogues was synthesized, which represented conformationally constrained analogues of miconazole (1). In vitro and vivo topical antifungal activity against both dermatophytes and candida species varied widely, but 13c proved to be significantly superior to both 1 and clotrimazole against a vaginal Candida infection in hamsters, while 13b was significantly more active than 1 against a a topical Trichophyton infection in guinea pigs. None of the compounds were orally active. When the most direct analogue of 1 proved to be among the least active, a molecular modeling study was done using 1, the two active analogues 13b and 13c, and the inactive analogue 13a. All four compounds possessed skeletally similar conformations either at or energetically readily accessible from the global minimum energy conformations. This common conformation of the inactive analogue 13a, however, occupies unique molecular volume space associated with two chlorine atoms, which must also present unique electrostatic properties at the receptor. The conformation-activity relationships discussed may contribute toward deduction of additional structural requirements for pharmacophore optimization and more efficacious antifungal drugs.

  DOI：

  10.1021/jm00100a030
• 作为产物：
  描述：

  Acetic acid 2-bromo-4,6-dichloro-benzyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以57%的产率得到2-bromo-4,6-dichlorobenzyl alcohol
  参考文献：
  名称：

  Isobenzofurans as conformationally constrained miconazole analogs with improved antifungal potency

  摘要：

  A series of halogen-substituted isobenzofuran analogues was synthesized, which represented conformationally constrained analogues of miconazole (1). In vitro and vivo topical antifungal activity against both dermatophytes and candida species varied widely, but 13c proved to be significantly superior to both 1 and clotrimazole against a vaginal Candida infection in hamsters, while 13b was significantly more active than 1 against a a topical Trichophyton infection in guinea pigs. None of the compounds were orally active. When the most direct analogue of 1 proved to be among the least active, a molecular modeling study was done using 1, the two active analogues 13b and 13c, and the inactive analogue 13a. All four compounds possessed skeletally similar conformations either at or energetically readily accessible from the global minimum energy conformations. This common conformation of the inactive analogue 13a, however, occupies unique molecular volume space associated with two chlorine atoms, which must also present unique electrostatic properties at the receptor. The conformation-activity relationships discussed may contribute toward deduction of additional structural requirements for pharmacophore optimization and more efficacious antifungal drugs.

  DOI：

  10.1021/jm00100a030

文献信息

• Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, process for preparing them, medicaments comprising these compounds, and their use
  申请人：JAEHNE Gerhard

  公开号：US20090215728A1

  公开（公告）日：2009-08-27

  This invention relates to arylaminoaryl-alkyl-substituted imidazolidone-2,4-diones of formula (I) and also to their physiologically tolerated salts: Wherein R, R′, R1 to R10, A, D, E, G, L and p are as defined herein. The invention also relates to processes for preparing them, pharmaceutical compositions comprising them and their therapeutic use. The compounds are suitable, for example, as anti-obesity drugs and for treating cardiometabolic syndrome.

  这项发明涉及公式（I）中的芳基氨基芳基烷基取代的咪唑烷二酮及其生理耐受的盐： 其中R、R'、R1至R10、A、D、E、G、L和p如本文所定义。该发明还涉及制备它们的方法、包含它们的药物组合物以及它们的治疗用途。这些化合物适用于例如作为抗肥胖药物和治疗心脏代谢综合征。
• 1-aryl-1-(1H-azol-1-ylalkyl)-1,3-dihydroisobenzofurans, related
  申请人：Schering Corporation

  公开号：US04737508A1

  公开（公告）日：1988-04-12

  Novel compounds including 1-aryl-1-(1H-imidazol-1-ylmethyl)-1,3-dihydroisobenzofurans such as 1-(4-chlorophenyl)-1-(1H-imidazol-1-ylmethyl)-1,3-dihydroisobenzofuran, and 1-aryl-1-(1H-1,2,4-trizazol-1-ylmethyl)-1,3-dihydroisobenzofurans are disclosed. The corresponding benzo[c]thiopenes, isochromans, and isothiochromans and antifungal pharmaceutical compositions containing same, and methods of using said pharmaceutical compositions to elicit an antifungal response in warm blooded animals having a susceptible antifungal infection are also disclosed.

  新型化合物包括1-芳基-1-(1H-咪唑-1-基甲基)-1,3-二氢异苯并呋喃类化合物，例如1-(4-氯苯基)-1-(1H-咪唑-1-基甲基)-1,3-二氢异苯并呋喃，以及1-芳基-1-(1H-1,2,4-三氮唑-1-基甲基)-1,3-二氢异苯并呋喃被披露。相应的苯并[c]噻吩、异色烯、异硫色烯和含有它们的抗真菌药物组合物，以及使用所述药物组合物在具有易感抗真菌感染的温血动物中引发抗真菌反应的方法也被披露。
• 1-Aryl-1-(1H-azol-1-ylalkyl)-1,3-dihydroisobenzofurans, related
  申请人：Schering Corporation

  公开号：US04877801A1

  公开（公告）日：1989-10-31

  Novel compounds including 1-aryl-1-(1H-imidazol-1-ylmethyl)-1,3-dihydroisobenzofurans such as 1-(4-chlorophenyl)-1-(1H-imidazol-1-ylmethyl)-1,3-dihydroisobenzofuran, and 1-aryl-1-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dihydroisobenzofurans are disclosed. The corresponding benzo[c]thiophenes, isochromans, and isothiochromans and antifungal pharmaceutical compositions containing same, and methods of using said pharmaceutical compositions to elicit an antifungal response in warm blooded animals having a susceptible antifungal infection are also disclosed.

  本发明揭示了包括1-芳基-1-(1H-咪唑-1-基甲基)-1,3-二氢异苯并呋喃类化合物，例如1-(4-氯苯基)-1-(1H-咪唑-1-基甲基)-1,3-二氢异苯并呋喃，以及1-芳基-1-(1H-1,2,4-三唑-1-基甲基)-1,3-二氢异苯并呋喃。还揭示了相应的苯并[c]噻吩，异色烷，和异硫烷以及含有它们的抗真菌药物组合物，以及使用该药物组合物在易感抗真菌感染的温血动物中引起抗真菌反应的方法。
• [DE] ARYLAMINOARYL-ALKYL-SUBSTITUIERTE IMIDAZOLIDIN-2,4-DIONE, VERFAHREN ZU IHRER HERSTELLUNG, DIESE VERBINDUNGEN ENTHALTENDE ARZNEIMITTEL UND IHRE VERWENDUNG<br/>[EN] ARYLAMINOARYL-ALKYL-SUBSTITUTED IMIDAZOLIDINE-2,4-DIONES, PROCESSES FOR PREPARING THEM, MEDICAMENTS COMPRISING THESE COMPOUNDS, AND THEIR USE<br/>[FR] IMIDAZOLIDIN-2,4-DIONE ARYLAMINOARYL-ALKYL-SUBSTITUÉE, SON PROCÉDÉ DE FABRICATION, MÉDICAMENT CONTENANT CE COMPOSÉ ET SON UTILISATION
  申请人：SANOFI AVENTIS

  公开号：WO2008017381A1

  公开（公告）日：2008-02-14

  (DE) Arylaminoaryl-alkyl-substituierte Imidazolidin-2,4-dione, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Arzneimittel und ihre Verwendung. Die Erfindung betrifft Verbindungen der Formel I, worin die Reste R und R' A, D, E, G, L, p und Rl bis RIO die angegebenen Bedeutungen haben, sowie deren physiologisch verträgliche Salze. Die Verbindungen eignen sich z.B. als Antiadiposita und zur Behandlung des cardio-metabolischen Syndroms.(EN) Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, processes for preparing them, medicaments comprising these compounds, and their use. The invention relates to compounds of the formula I in which the radicals R and R', A, D, E, G, L, p and R1 to R1O have the stated definitions, and also to their physiologically tolerated salts. The compounds are suitable, for example, as anti-obesity drugs and for treating cardiometabolic syndrome.(FR) L'invention concerne des composés de formule I, dans laquelle les radicaux R et R', A, D, E, G, L, p et R1 à R10 ont les significations données, ainsi que leurs sels physiologiquement acceptables. Les composés s'utilisent par ex. comme agent anti-obésité et pour le traitement du syndrome cardio-métabolique.

  （德）芳氨基芳烷基取代的二氢咪唑-2,4-二酮，制备它们的方法，含有这些化合物的药物以及它们的用途。本发明涉及式I的化合物，其中基团R和R'，A、D、E、G、L、p及R1至RIO具有所述的定义，以及它们的生理上可耐受的盐。这些化合物适用于例如作为抗脂肪过度积累剂，用于治疗心肌代谢综合征。 （英文参考翻译）芳氨基芳烷基取代的二氢咪唑-2,4-二酮，制备它们的方法，含有这些化合物的药物以及它们的用途。本发明涉及式I的化合物，其中基团R和R'，A、D、E、G、L、p及R1至RIO具有所述的定义，以及它们的生理上可耐受的盐。这些化合物适用于例如作为抗脂肪过度积累剂，用于治疗心肌代谢综合征。
• LOVEY, RAYMOND G.;ELLIOTT, ARTHUR J.
  作者：LOVEY, RAYMOND G.、ELLIOTT, ARTHUR J.

  DOI：——

  日期：——