7-bromo-3-methoxy-2-naphthoic acid chloride | 123266-52-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 7-bromo-3-methoxy-2-naphthoic acid chloride
• 英文别名: 7-bromo-3-methoxy-2-naphthoyl chloride；7-Bromo-3-methoxynaphthalene-2-carbonyl chloride
• CAS: 123266-52-4
• 化学式: C₁₂H₈BrClO₂
• 分子量: 299.551
• InChiKey: HMBKOYJFCMRZME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-bromo-3-methoxy-2-naphthoic acid chloride 以 盐酸 、 氯仿 为溶剂， 以81%的产率得到S-7-Bromo-3-methoxy-N[(1-ethyl-2-pyrrolidinyl)methyl]naphthyl-2-carboxamide
  参考文献：
  名称：

  Dopamine receptor ligands and imaging agents

  摘要：

  小说CNS多巴胺D-2受体，例如化合物5-碘-7-N-[(1-乙基-2-吡咯烷基)甲基]羧酰胺-2,3-二氢苯并呋喃，已经披露。这些化合物可用作人类大脑中D-2受体的成像剂，并表现出良好的大脑保留和体内稳定性。

  公开号：

  US05122361A1
• 作为产物：
  描述：

  methyl 7-bromo-3-methoxy-2-naphthoate 在 sodium hydroxide 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 5.0h， 生成 7-bromo-3-methoxy-2-naphthoic acid chloride
  参考文献：
  名称：

  Synthesis and characterization of iodobenzamide analogs: potential D-2 dopamine receptor imaging agents

  摘要：

  (S)-N-[(1-Ethyl-2-pyrrolidinyl)methyl]-2-hydroxy-3-iodo-6- methoxybenzamide ([123I]IBZM) is a central nervous system (CNS) D-2 dopamine receptor imaging agent. In order to investigate the versatility of this parent structure in specific dopamine receptor localization and the potential for developing new dopamine receptor imaging agents, a series of new iodinated benzamides with fused ring systems, naphthalene (INAP) and benzofuran (IBF), was synthesized and radiolabeled, and the in vivo and in vitro biological properties were characterized. The best analogue of IBZM is IBF (21). The specific binding of [125I]IBF (21) with rat striatal tissue preparation was found to be saturable and displayed a Kd of 0.106 +/- 0.015 nM. Competition data of various receptor ligands for [125I]IBF (21) binding show the following rank order of potency: spiperone greater than IBF (21) greater than IBZM greater than (+)-butaclamol greater than (+/-)-ADTN,6,7 greater than ketanserin greater than SCH-23390 much greater than propranolol. The in vivo biodistribution results confirm that [125I]IBF (21) concentrated in the striatal area after iv injection into rats. The study demonstrates that [123I]IBF (21) is a potential agent for imaging CNS D-2 dopamine receptors.

  DOI：

  10.1021/jm00163a029

文献信息

• Synthesis and cytotoxic activity of benzo[a]acronycine and benzo[b]acronycine substituted on the A ring
  作者：Thomas Gaslonde、Fabiola Covello、Laura Velazquez-Alonso、Stéphane Léonce、Alain Pierré、Bruno Pfeiffer、Sylvie Michel、François Tillequin

  DOI：10.1016/j.ejmech.2011.02.050

  日期：2011.5

  The impact of substitutions at position 10 in the A ring of the cytotoxic benzo[a]acronycine and benzo[b]acronycine series has been explored. 10-Bromobenzo[a] and 10-bromobenzo[b]acronycine were prepared in 12% and 15% yield respectively from commercially available chemicals. Their 1,2-dihydro-1,2-dihydroxy diesters were synthesized. The different derivatives were tested against two cell lines KB-3-1

  已经研究了细胞毒性苯并[ a ]阿卡洛霉素和苯并[ b ]阿卡洛霉素系列的A环上第10位取代的影响。由市售化学品分别以12％和15％的收率制备10-溴苯并[ a ]和10-溴苯并[ b ]阿卡那霉素。合成了它们的1，2-二氢-1，2-二羟基二酯。针对两种细胞系KB-3-1和L1210测试了不同的衍生物。发现它们的细胞毒性活性与其未取代的对应物在相同的范围内。这些结构-活性关系可以得出结论，即在10位上引入取代基可以保持苯并[ a ]和[ b ]的活性。]强力霉素系列产品，为进一步的药物调节开辟了道路。
• MURPHY, RAYMOND A.;KUNG, HANK F.;KUNG, MEI-PING;BILLINGS, JEFFREY, J. MED. CHEM., 33,(1990) N, C. 171-178
  作者：MURPHY, RAYMOND A.、KUNG, HANK F.、KUNG, MEI-PING、BILLINGS, JEFFREY

  DOI：——

  日期：——
• US5122361A
  申请人：——

  公开号：US5122361A

  公开（公告）日：1992-06-16
• Synthesis and characterization of iodobenzamide analogs: potential D-2 dopamine receptor imaging agents
  作者：Raymond A. Murphy、Hank F. Kung、Mei Ping Kung、Jeffrey Billings

  DOI：10.1021/jm00163a029

  日期：1990.1

  (S)-N-[(1-Ethyl-2-pyrrolidinyl)methyl]-2-hydroxy-3-iodo-6- methoxybenzamide ([123I]IBZM) is a central nervous system (CNS) D-2 dopamine receptor imaging agent. In order to investigate the versatility of this parent structure in specific dopamine receptor localization and the potential for developing new dopamine receptor imaging agents, a series of new iodinated benzamides with fused ring systems, naphthalene (INAP) and benzofuran (IBF), was synthesized and radiolabeled, and the in vivo and in vitro biological properties were characterized. The best analogue of IBZM is IBF (21). The specific binding of [125I]IBF (21) with rat striatal tissue preparation was found to be saturable and displayed a Kd of 0.106 +/- 0.015 nM. Competition data of various receptor ligands for [125I]IBF (21) binding show the following rank order of potency: spiperone greater than IBF (21) greater than IBZM greater than (+)-butaclamol greater than (+/-)-ADTN,6,7 greater than ketanserin greater than SCH-23390 much greater than propranolol. The in vivo biodistribution results confirm that [125I]IBF (21) concentrated in the striatal area after iv injection into rats. The study demonstrates that [123I]IBF (21) is a potential agent for imaging CNS D-2 dopamine receptors.
• Dopamine receptor ligands and imaging agents
  申请人：Trustees of the University of Pennsylvania

  公开号：US05122361A1

  公开（公告）日：1992-06-16

  Novel CNS dopamine D-2 receptors, such as the compound 5-iodo-7-N-[(1-ethyl-2-pyrrolidinyl)methyl]carboxamide-2,3-dihydrobenzofur an, are disclosed. These compounds are useful as imaging agents for D-2 receptors in the human brain and exhibit good brain retention and in vivo stability.

  小说CNS多巴胺D-2受体，例如化合物5-碘-7-N-[(1-乙基-2-吡咯烷基)甲基]羧酰胺-2,3-二氢苯并呋喃，已经披露。这些化合物可用作人类大脑中D-2受体的成像剂，并表现出良好的大脑保留和体内稳定性。