2-羟基-5-硝基苯甲酸乙酯 | 42348-40-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-羟基-5-硝基苯甲酸乙酯
• 英文名称: ethyl 5-nitrosalicylate
• 英文别名: ethyl 2-hydroxy-5-nitrobenzoate
• CAS: 42348-40-3
• 化学式: C₉H₉NO₅
• mdl: MFCD01365750
• 分子量: 211.174
• InChiKey: KPDLTBYCZXVKQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5-硝基水杨酸	5-Nitrosalicylic acid	96-97-9	C7H5NO5	183.12
  间硝基苯甲酸乙酯	ethyl-3-nitrobenzoate	618-98-4	C9H9NO4	195.175
  水杨酸乙酯	2-hydroxy-benzoic acid ethyl ester	118-61-6	C9H10O3	166.177

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  乙基2-甲氧基-5-硝基苯甲酸酯	ethyl 2-methoxy-5-nitrobenzoate	90923-08-3	C10H11NO5	225.201
  ——	benzyl 2-hydroxy-5-nitrobenzoate	155388-71-9	C14H11NO5	273.245
  5-硝基水杨酸	5-Nitrosalicylic acid	96-97-9	C7H5NO5	183.12
  5-氨基-2-羟基苯甲酸乙酯	ethyl 5-aminosalicylate	62773-65-3	C9H11NO3	181.191
  ——	2-ethoxycarbonylmethoxy-5-nitro-benzoic acid ethyl ester	91958-81-5	C13H15NO7	297.265
  ——	2-allyloxy-5-nitrobenzoic acid	301653-20-3	C10H9NO5	223.185
  ——	2-benzyloxy-5-nitrobenzoic acid	874523-84-9	C14H11NO5	273.245
  ——	5-Amino-2-methoxymethoxy-benzoic acid ethyl ester	179911-54-7	C11H15NO4	225.244
  ——	4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3-ethoxycarbonylnitrobenzene	337520-12-4	C19H26N2O7	394.425
  2-羟基-5-硝基苯甲酰胺	2-hydroxy-5-nitrobenzamide	2912-78-9	C7H6N2O4	182.136

反应信息

• 作为反应物：
  描述：

  2-羟基-5-硝基苯甲酸乙酯 在 氢氧化钾 、 potassium carbonate 、 丁酮 、 sodium iodide 作用下， 生成 5-硝基水杨酸
  参考文献：
  名称：

  The Effect of Heat on the β-Naphthylmethyl and the 9-Phenanthrylmethyl Ether of 3,5-Dichlorosalicylic Acid

  摘要：

  DOI：

  10.1021/ja01251a038
• 作为产物：
  描述：

  水杨酸乙酯 在 硝酸 、 溶剂黄146 作用下， 生成 2-羟基-5-硝基苯甲酸乙酯
  参考文献：
  名称：

  Onset of spinal block is more rapid with isobaric than hyperbaric bupivacaine

  摘要：

  Purpose: To compare isobaric with hyperbaric 9.75 mg bupivacaine injected intrathecally, and to evaluate the effects of subsequent injection of lidocaine 2% into the epidural space.Methods: Patients in group I (n = 30) received isobaric 9.75 mg bupivacaine and in group 2 (n = 30) hyperbaric 9.75 mg bupivacaine injected into the subarachnoid space in a combined spinal-epidural technique, They were undergoing urological, gynecological, orthopedic, gastro-intestinal or vascular surgery. Using a double blind technique, the followings parameters were measured: cutaneous analgesia to pinprick, motor blockade, time for two segment regression, time for complete regression of the motor block, quality of anesthesia. In 12 patients the effect of epidural injections of 3 ml lidocaine 2% was observed.Results: Motor and sensory block developed more rapidly (five minutes) in the isobaric group (P < 0.05). Maximum upper level (T7 +/- 2), two-segment regression (52 min in both groups), motor recovery (160 vs 157 min), and quality of anesthesia did not differ between the two groups. Thirty nine epidural injections of 3 mi lidocaine 2% were given in 12 patients 10 min after spinal injection, 28 were in the hyperbaric group (P < 0.05). Twenty six of the epidural injections produced an increase in sensory block of 0 or 1 dermatome, and 13, of 2 or more.Conclusion: The block developed more rapidly in the isobaric group, but both isobaric and hyperbaric 9.75 mg bupivacaine produced adequate upper levels of analgesia for surgery. The effect of epidural injections of 3 mi lidocaine 2% was usually minimal.

  DOI：

  10.1007/bf03020730

文献信息

• Benzoxazepinones and their use as squalene synthase inhibitors
  申请人：——

  公开号：US20030078251A1

  公开（公告）日：2003-04-24

  There is disclosed a compound represented by the formula [I]: 1 wherein R 1 is optionally substituted 1-carboxyethyl group, optionally substituted alkyl-sulfonyl group, optionally substituted (carboxy-cycloalkyl)-alkyl group, —X 1 —X 2 —Ar—X 3 —X 4 —COOH (wherein X 1 and X 4 are a bond or alkylene group, X 2 and X 3 are a bond, —O—, —S—, Ar is divalent aromatic group etc.), R 2 is alkyl group optionally substituted with alkanoyloxy group and/or hydroxy group, R 3 is alkyl group, and W is halogen atom, etc., or a salt thereof. The compound has the cholesterol lowering activity and the triglyceride lowering activity and is useful for preventing and/or treating hyperlipidemia.

  披露了一种由公式[I]表示的化合物： 1 其中R 1 是可选地取代的1-羧乙基，可选地取代的烷基亚磺酰基，可选地取代的(羧基环烷基)-烷基，—X 1 —X 2 —Ar—X 3 —X 4 —COOH(其中X 1 和X 4 是键或亚烷基，X 2 和X 3 是键，—O—，—S—，Ar是二价芳香族等)，R 2 是可选地由酰氧基和/或羟基取代的烷基，R 3 是烷基，W是卤素原子等，或其盐。该化合物具有降低胆固醇活性和降低甘油三酯活性，用于预防或治疗高脂血症。
• Biphenyl derivatives
  申请人：Eisai Co., Ltd.

  公开号：US05849912A1

  公开（公告）日：1998-12-15

  A biphenyl derivative represented by the following formula (I) or a pharmacologically acceptable salt thereof: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are defined in the specification, is clinically useful for treating and ameliorating mental disorders such as cerebrovascular disorder, aggressive behavior due to senile dementia, mental excitation, poriomania, delirium, hallucination, hyperkinesia, schizophrenia, emotional disturbance, depression, neurosis, psychophysiologic disorder and anxiety neurosis. The compounds exhibit dopamine 2 receptor antagonism and/or serotonin 2 receptor antagonism.

  以下是公式（I）所代表的联苯衍生物或其药理学上可接受的盐：##STR1##其中R.sup.1、R.sup.2、R.sup.3、R.sup.4和R.sup.5在规范中有定义，对于治疗和改善脑血管疾病、老年性痴呆引起的攻击性行为、精神兴奋、狂躁症、幻觉、多动症、精神分裂症、情绪紊乱、抑郁症、神经症、心理生理障碍和焦虑症等精神障碍具有临床上的用途。这些化合物表现出多巴胺2受体拮抗作用和/或5-羟色胺2受体拮抗作用。
• Cinnamyl Derivatives: Synthesis and Factor Xa (FXa) Inhibitory Activities
  作者：Tetsuji Noguchi、Naoki Tanaka、Toyoki Nishimata、Riki Goto、Miho Hayakawa、Atsuhiro Sugidachi、Taketoshi Ogawa、Fumitoshi Asai、Koichi Fujimoto

  DOI：10.1248/cpb.56.758

  日期：——

  To develop a potent and oral anticoagulant, a series of compounds with cinnamyl moiety was synthesized and their factor Xa (FXa) inhibitory activities were examined. As a result, some cinnamyl derivatives showed potent FXa inhibitory activities in vitro. Among them, compounds with substituent at the 3-position on the central benzene ring represented by (N-4-[1-(acetimidoyl)piperidin-4-yloxy]-3-chlorophenyl}-N-[(E)-3-(3-amidinophenyl)-2-propenyl]sulfamoyl)acetic acid dihydrochloride (45b) and (N-4-[1-(acetimidoyl)piperidin-4-yloxy]-3-carbamoylphenyl}-N-[(E)-3-(3-amidinophenyl)-2-propenyl]sulfamoyl)acetic acid dihydrochloride (45j) exhibited potent FXa inhibitory activities with IC50 values of less than 10 nM in vitro. These compounds also showed potent anticoagulant activities both in vitro and ex vivo. Furthermore, these compounds exhibited no lethal toxicity (30 mg/kg, i.v.).

  为了开发一种强效且可通过口服给药的抗凝剂，合成了一系列含有肉桂基部分的化合物，并检测了它们对因子Xa (FXa)的抑制活性。结果显示，一些肉桂基衍生物具有强效的FXa体外抑制活性。在这些化合物中，含有取代基位于中心苯环3-位的化合物，如(N-4-[1-(乙酰亚胺基)哌啶-4-氧基]-3-氯苯基}-N-[(E)-3-(3-氨基苯基)-2-丙烯基]磺酰胺)乙酸二盐酸盐(45b)和(N-4-[1-(乙酰亚胺基)哌啶-4-氧基]-3-羧酰胺苯基}-N-[(E)-3-(3-氨基苯基)-2-丙烯基]磺酰胺)乙酸二盐酸盐(45j)，表现出强效的FXa抑制活性，其IC50值在体外小于10 nM。这些化合物在体外和体外实验中均显示出强效的抗凝活性。此外，这些化合物没有致命毒性(30 mg/kg，静脉注射)。
• Benzamidine derivatives
  申请人：Sankyo Company, Limited

  公开号：US06555556B1

  公开（公告）日：2003-04-29

  Benzamidine derivatives of formula (I) or pharmaceutically acceptable salts thereof exhibit excellent inhibitory activity against factor Xa and are useful for treating or preventing blood coagulation disorders: wherein R1 represents a hydrogen atom, a halogen atom, an alkyl group or a hydroxyl group; R2 represents a hydrogen atom, a halogen atom or an alkyl group, R3 represents a hydrogen atom, an optionally substituted alkyl group, an aralkyl group, an optionally substituted alkanoyl group or an optionally substituted alkylsulfonyl group, R4 and R5 are the same as or different from each other and each represent a hydrogen atom, a halogen atom, an optionally substituted alkyl group, an alkoxy group, a carboxyl group, an alkoxycarbonyl group or an optionally substituted carbamoyl group, and R6 represents a substituted pyrrolidine group or substituted piperidine group.

  Benzamidine衍生物的化学式(I)或其药学上可接受的盐对Xa因子表现出优异的抑制活性，并且可用于治疗或预防血液凝固紊乱：其中R1代表氢原子、卤素原子、烷基或羟基；R2代表氢原子、卤素原子或烷基，R3代表氢原子、可选择取代的烷基、芳基烷基、可选择取代的烷酰基或可选择取代的烷基磺酰基，R4和R5彼此相同或不同，各自代表氢原子、卤素原子、可选择取代的烷基、烷氧基、羧基、烷氧羰基或可选择取代的氨基羰基，R6代表取代的吡咯烷基或取代的哌啶基。
• A Convenient Method for Synthesizing Modified 4-Nitrophenols
  作者：Yumi Nakaike、Yoshio Kamijo、Satoshi Mori、Mina Tamura、Nagatoshi Nishiwaki、Masahiro Ariga

  DOI：10.1021/jo0516990

  日期：2005.11.1

  β-Nitroenamine having a formyl group behaves as the synthetic equivalent of unstable nitromalonaldehyde upon treatment with ketones under basic conditions and leads to 2,6-disubstituted 4-nitrophenols. The present method is safer than the conventional one using sodium nitromalonaldehyde and enables the preparation of hitherto unknown nitrophenols.

  具有甲酰基的β-亚硝胺在碱性条件下用酮处理时表现为不稳定的亚硝基苯甲醛的合成当量，并导致2，6-二取代的4-硝基苯酚。本方法比使用次氮醛甲醛钠的常规方法更安全，并且能够制备迄今未知的硝基酚。