TRANS-4-GUANIDINOMETHYLCYCLOHEXANECARBOXYLIC ACID HYDROCHLORIDE | 78718-15-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: TRANS-4-GUANIDINOMETHYLCYCLOHEXANECARBOXYLIC ACID HYDROCHLORIDE
• 英文别名: trans-4-guanidinomethylcyclohexanecarboxylic acid
• CAS: 78718-15-7
• 化学式: C₉H₁₇N₃O₂*ClH
• 分子量: 235.714
• InChiKey: QCVUPSYRZFNUBN-MEZFUOHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  99.2
• 氢给体数：
  4.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  TRANS-4-GUANIDINOMETHYLCYCLOHEXANECARBOXYLIC ACID HYDROCHLORIDE 在 氯化亚砜 作用下， 生成 trans-4-guanidinomethylcyclohexanecarboxylic acid chloride hydrochloride
  参考文献：
  名称：

  Cyclohexane carboxylic acid derivatives

  摘要：

  化合物的式子为：##STR1## 其中，R1代表vanilyl，naphthyl，pyridyl或α-生育酚基团，或者是式子##STR2## 其中，R2代表氢原子，低烷氧基，甲酰基，低烷酰基或苯基团，或者是式子--(CH2)nCOOR3，其中，R3代表氢原子，低烷基，苯基，苄基，苯氧羰基甲基基团，n代表0到2的整数，或其药学上可接受的盐，可用作抗溃疡剂。

  公开号：

  US04348410A1

文献信息

• Phenylalanine derivative and proteinase inhibitor
  申请人：Okamoto, Shosuke

  公开号：EP0284632A1

  公开（公告）日：1988-10-05

  A phenylalanine derivative having the formula (I): wherein A represents (a) H2N-, (b) or B represents (a) (b) or wherein m is 0, 1, or 2 and n is 3, 4, or 5; X represents (a) hydroxy, (b) nitro, (c) amino, (d) phenoxy which may be substituted with (i) halogen or (ii) nitro, (e) C1-C4 alkyloxy which may be substituted with (i) phenyl or (ii) benzoyl, (f) benzoyl, (g) pyridyloxy which may be substituted with (i) halogen or (ii) nitro, or (h) C1-C4 alkyl which may be substituted with halogen; Y represents or -OR3 wherein R1 and R2 are independently (a) hydrogen, (b) phenyl which may be substituted with (i) benzoyl, (ii) C1-C4 alkylcarbonyl, (iii) C1-C4 alkyl which may be further substituted with C1-C4 alkoxycarbonyl or hydroxycarbonyl, (iv) C2-Cs alkenyl which may be further substituted with hydroxycarbonyl or C1-C4 alkoxycarbonyl, (v) C1-C4 alkoxycarbonyl, or (vi) amidino, (c) pyridyl which may be substituted with halogen or carboxyl (d) imidazolyl, (e) pyrimidyl, (f) tetrazolyl, (g) thiazolyl which may be substituted with C,-C4 alkyl which may be further substituted with C1-C4 alkoxycarbonyl, (h) C1-C6 alkyl which may be substituted with C1-C4 alkoxy, C1-C4 alkoxycarbonyl, phenyl, or benzoyl, (i) CS-C7 cycloalkyl which may be substituted with C1-C4 alkoxycarbonyl or (j) R' and R2 may form, with the nitrogen atom attached thereto, (i) pyperazyl which may be substituted on the nitrogen atom with C1-C4 alkyl which may be further substituted with phenyl, (ii) piperidino which may be substituted with carboxyl or C1-C4 alkoxycarbonyl, (iii) pyrrolidyl which may be substituted with C1-C4 alkoxycarbonyl, or (iv) morpholyl; and R3 represents (a) hydrogen, (b) C1-C6 alkyl which may be substituted with (i) C1-C4 alkoxy, (ii) phenyl, or (iii) pyridyl, or (c) pyridyl; or a pharmaceutically acceptable acid salt thereof. This phenylalanine derivative is effective as a proteinase.

  具有以下式（I）的苯丙氨酸衍生物：其中A代表（a）H2N-，（b）或B代表（a）（b）或其中m为0、1或2，n为3、4或5；X代表（a）羟基，（b）硝基，（c）氨基，（d）苯氧基，其可以被（i）卤素或（ii）硝基取代，（e）C1-C4烷氧基，其可以被（i）苯基或（ii）苯甲酰基取代，（f）苯甲酰基，（g）吡啶氧基，其可以被（i）卤素或（ii）硝基取代，或（h）C1-C4烷基，其可以被卤素取代；Y代表或-OR3，其中R1和R2独立地为（a）氢，（b）苯基，其可以被（i）苯甲酰基，（ii）C1-C4烷基羰基，（iii）C1-C4烷基，其可以进一步被C1-C4烷氧羰基或羟基羰基取代，（iv）C2-Cs烯烃基，其可以进一步被羟基羰基或C1-C4烷氧羰基取代，（v）C1-C4烷氧羰基，或（vi）酰胺基，（c）吡啶基，其可以被卤素或羧基取代（d）咪唑基，（e）嘧啶基，（f）四唑基，（g）噻唑基，其可以被C1-C4烷基取代，其可以进一步被C1-C4烷氧羰基取代，（h）C1-C6烷基，其可以被C1-C4烷氧基，C1-C4烷氧羰基，苯基或苯甲酰基取代，（i）C5-C7环烷基，其可以被C1-C4烷氧羰基取代或（j）R'和R2可以与其连接的氮原子形成（i）哌嗪基，其可以在氮原子上被C1-C4烷基取代，其可以进一步被苯基取代，（ii）哌啶基，其可以被羧基或C1-C4烷氧羰基取代，（iii）吡咯基，其可以被C1-C4烷氧羰基取代，或（iv）吗啉基；R3代表（a）氢，（b）C1-C6烷基，其可以被（i）C1-C4烷氧基，（ii）苯基或（iii）吡啶基取代，或（c）吡啶；或其药学上可接受的酸盐。该苯丙氨酸衍生物作为蛋白酶具有有效性。
• Medicinal chemical studies on synthetic protease inhibitors, trans-4-guanidinomethylcyclohexanecarboxylic acid aryl esters.
  作者：TOSHIO SATOH、MUTUMI MURAMATU、YASUHIRO OOI、HIDEKI MIYATAKA、TOSHIO NAKAJIMA、MASANORI UMEYAMA

  DOI：10.1248/cpb.33.647

  日期：——

  trans-4-Guanidinomethylcyclohexanecarboxylic acid (trans-GMCHA) aryl esters were synthesized and tested for inhibitory effects on serine proteases, trypsin, chymotrypsin, plasmin, plasma kallikrein, pancreatic kallikrein, urokinase and thrombin. In general, these compounds showed strong inhibitory effects on chymotrypsin, pancreatic kallikrein and urokinase, but the effects varied greatly depending on the substituent in the benzene nucleus. Some of the trans-GMCHA aryl esters strongly inhibited compound 48/80-induced histamine release from mast cells / the p-tert-butylphenyl ester was especially active.

  合成了trans-4-氨基甲基环己甲酸(trans-GMCHA)的芳香酯，并测试了其对丝氨酸蛋白酶的抑制作用，包括胰蛋白酶、糜蛋白酶、纤溶酶、血浆激肽酶、胰腺激肽酶、尿激酶和凝血酶。总体而言，这些化合物对糜蛋白酶、胰腺激肽酶和尿激酶显示出强烈的抑制作用，但效果在很大程度上取决于苯核中的取代基。一些trans-GMCHA芳香酯显著抑制了化合物48/80诱导的肥大细胞组胺释放，其中对酚-tert-丁基酚酯的活性尤其强。
• Cyclohexane carbocyclic ester derivative and cyclodextrin complex and composition for treatment of helicobacter pylori infections
  申请人：Teikoku Chemical Industries Co., Ltd.

  公开号：US06444703B1

  公开（公告）日：2002-09-03

  The present invention relates to a pharmaceutical composition which is appropriate for eradication or extermination of Helicobacter pylori wherein [4-[4-(4-methylbenzyloxycarbonyl)phenyl[phenyl trans-4-guanidinomethylcyclohexanecarboxylate or an acid addition salt thereof are compounded and it also relates to a complex consisting them.

  本发明涉及一种适用于根除或消灭幽门螺杆菌的药物组合物，其中包含4-[4-(4-甲基苯甲氧羰基)苯基]苯基转-4-胍甲基环己烷羧酸盐或其酸加成盐，同时还涉及由它们组成的复合物。
• Syntheses and Inhibitory Effects on Gastric Lesions of trans-Guanidinomethylcyclohexane Carboxylic Acid Arylamides.
  作者：Hiroki UEDA、Yuji MOMOI、Tetsuyuki IKEDA、Hisao KAKEGAWA、Hideki MIYATAKA、Hitoshi MATSUMOTO、Toshio SATOH

  DOI：10.1248/cpb.41.522

  日期：——

  A novel series of trans-guanidinomethylcyclohexanecarboxylic acid (trans-GMCHA) arylamides was synthesized.The several trans-GMCHA arylamide derivatives showed more potent inhibitory effects on the stress- and HCl-ethanol-induced gastric ulcers than cetraxate in rats. In acute toxicity studies in mice, most amides showed such severe toxicity that all mice injected with these compounds (50 mg/kg, i.p.) died. However, mice injected with the trans-GMCHA (2', 3'- and 4'-ethoxycarboxy)phenylamide (7, 8 and 9) which bear an alkyloxycarbonyl group at benzene ring survived.From these results, trans-GMCHA (2'-ethoxycarbonyl)phenylamide (7) was selected as a promising anti-ulcer agent.

  研究人员合成了一系列新型的反式胍基甲基环己烷羧酸（反式 GMCHA）芳基酰胺，其中几种反式 GMCHA 芳基酰胺衍生物对压力和盐酸乙醇诱发的大鼠胃溃疡的抑制作用比四己酸盐更强。在对小鼠进行的急性毒性研究中，大多数酰胺类化合物都显示出严重的毒性，注射这些化合物（50 毫克/千克，静脉注射）的小鼠全部死亡。然而，注射了反式-GMCHA（2'、3'和 4'-乙氧基羰基）苯甲酰胺（7、8 和 9）的小鼠却存活了下来，因为这些化合物在苯环上带有一个烷氧基羰基。
• Novel guanidinomethylcyclohexanecarboxylic acid compounds and anti-ulcer
  申请人：Kanebo, Ltd.

  公开号：US04681895A1

  公开（公告）日：1987-07-21

  Novel N-phenyl-trans-4-guanidinomethylcyclohexanecarboxamide compounds of the formula: ##STR1## wherein R is hydrogen atom or a lower alkyl group, or a pharmaceutically acceptable salt thereof, which have excellent anti-ulcer activities and hence are useful as an anti-ulcer drug, and a pharmaceutical composition useful for the treatment and prophylaxis of peptic ulcers which comprises as an active ingredient the compound as set forth above in admixture with a conventional pharmaceutically acceptable carrier or diluent.

  该专利涉及一种新型N-苯基-转-4-胍甲基环己烷羧酰胺化合物，其化学式为：##STR1## 其中R为氢原子或较低的烷基，或其药学上可接受的盐。该化合物具有出色的抗溃疡活性，因此可用作抗溃疡药物。此外，该专利还涉及一种药物组合物，可用于治疗和预防消化性溃疡，其活性成分为上述化合物，与传统的药学可接受的载体或稀释剂混合。